K Nicolaou

Summary

Affiliation: The Scripps Research Institute
Country: USA

Publications

  1. ncbi request reprint Total synthesis of platensimycin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 45:7086-90. 2006
  2. pmc Synthesis and biological evaluation of new paclitaxel analogs and discovery of potent antitumor agents
    Kyriacos C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Org Biomol Chem 11:4154-63. 2013
  3. pmc General synthetic approach to functionalized dihydrooxepines
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
    Org Lett 15:1994-7. 2013
  4. pmc Synthesis of the C'D'E'F' domain of maitotoxin
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
    J Am Chem Soc 133:214-9. 2011
  5. doi request reprint The emergence of the structure of the molecule and the art of its synthesis
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 52:131-46. 2013
  6. doi request reprint A total synthesis trilogy: calicheamicin γ1(I), Taxol®, and brevetoxin A
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, USA
    Chem Rec 12:407-41. 2012
  7. pmc Synthesis of macroheterocycles through intramolecular oxidative coupling of furanoid β-ketoesters
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 51:4726-30. 2012
  8. ncbi request reprint A catalytic asymmetric three-component 1,4-addition/aldol reaction: enantioselective synthesis of the spirocyclic system of vannusal A
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:3874-9. 2005
  9. ncbi request reprint Total synthesis and biological evaluation of halipeptins A and D and analogues
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA
    J Am Chem Soc 128:4460-70. 2006
  10. ncbi request reprint Total synthesis and structural elucidation of azaspiracid-1. Final assignment and total synthesis of the correct structure of azaspiracid-1
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 128:2859-72. 2006

Research Grants

  1. TOTAL SYNTHESIS OF AZASPIRACIDS
    K Nicolaou; Fiscal Year: 2006
  2. TOTAL SYNTHESIS OF AZADIRACHTIN
    K Nicolaou; Fiscal Year: 2007
  3. SYNTHESIS OF ANTIBIOTICS
    K Nicolaou; Fiscal Year: 2007
  4. TOTAL SYNTHESIS OF KINAMYCINS AND LOMAIVITICINS
    K Nicolaou; Fiscal Year: 2007
  5. Synthesis of Marine Neurotoxins
    K Nicolaou; Fiscal Year: 2007
  6. SYNTHESIS OF ANTICANCER AGENTS
    K C Nicolaou; Fiscal Year: 2010
  7. SYNTHESIS OF ANTIBIOTICS
    K C Nicolaou; Fiscal Year: 2010
  8. TOTAL SYNTHESIS OF THIOSTREPTON
    K Nicolaou; Fiscal Year: 2005
  9. TOTAL SYNTHESIS OF NATURAL PRODUCTS
    K Nicolaou; Fiscal Year: 2002
  10. TOTAL SYNTHESIS OF APOPTOLIDIN
    K Nicolaou; Fiscal Year: 2004

Detail Information

Publications111 found, 100 shown here

  1. ncbi request reprint Total synthesis of platensimycin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 45:7086-90. 2006
  2. pmc Synthesis and biological evaluation of new paclitaxel analogs and discovery of potent antitumor agents
    Kyriacos C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Org Biomol Chem 11:4154-63. 2013
    ....
  3. pmc General synthetic approach to functionalized dihydrooxepines
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
    Org Lett 15:1994-7. 2013
    ..This approach features a regioselective Baeyer-Villiger oxidation and subsequent functionalization via the corresponding enol phosphate intermediate...
  4. pmc Synthesis of the C'D'E'F' domain of maitotoxin
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
    J Am Chem Soc 133:214-9. 2011
    ..X-ray crystallographic analysis of 6 provided unambiguous proof of its structure...
  5. doi request reprint The emergence of the structure of the molecule and the art of its synthesis
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 52:131-46. 2013
    ..This Essay traces the understanding of the structure of the molecule, the emergence of organic synthesis, and the art of total synthesis from the 19th century to the present day...
  6. doi request reprint A total synthesis trilogy: calicheamicin γ1(I), Taxol®, and brevetoxin A
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, USA
    Chem Rec 12:407-41. 2012
    ..Detailed behind-the-scenes accounts of the total syntheses of calicheamicin γ(1)(I), Taxol(®), and brevetoxin A are discussed with particular emphasis placed on strategies and tactics employed in these campaigns...
  7. pmc Synthesis of macroheterocycles through intramolecular oxidative coupling of furanoid β-ketoesters
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 51:4726-30. 2012
  8. ncbi request reprint A catalytic asymmetric three-component 1,4-addition/aldol reaction: enantioselective synthesis of the spirocyclic system of vannusal A
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:3874-9. 2005
  9. ncbi request reprint Total synthesis and biological evaluation of halipeptins A and D and analogues
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA
    J Am Chem Soc 128:4460-70. 2006
    ....
  10. ncbi request reprint Total synthesis and structural elucidation of azaspiracid-1. Final assignment and total synthesis of the correct structure of azaspiracid-1
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 128:2859-72. 2006
    ..In addition to the total synthesis of azaspiracid-1 (1), the syntheses of its C(1)-C(20) epimer (2) and of several truncated analogues for biological investigations are described...
  11. doi request reprint Total synthesis and biological evaluation of the resveratrol-derived polyphenol natural products hopeanol and hopeahainol A
    K C Nicolaou
    Chemical Synthesis Laboratory at Biopolis, Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 132:7540-8. 2010
    ..Biological evaluation of the synthesized compounds confirmed the reported acetylcholinesterase inhibitory activity of hopeahainol A (3) but not the reported cytotoxic potencies of hopeanol (2)...
  12. doi request reprint Total synthesis of echinopines A and B
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 132:3815-8. 2010
    ..Their total synthesis involves a novel intramolecular rhodium-catalyzed cyclopropanation (4 --> 16) and a samarium diiodide-mediated ring closure (3 --> 37)...
  13. ncbi request reprint Total synthesis of (+)-rugulosin and (+)-2,2'-epi-cytoskyrin A through cascade reactions
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:7917-21. 2005
  14. ncbi request reprint Discovery of a biologically active thiostrepton fragment
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    J Am Chem Soc 127:15042-4. 2005
    ....
  15. ncbi request reprint Synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with Dess-Martin periodinane
    K C Nicolaou
    Department of Chemistry, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Angew Chem Int Ed Engl 44:5992-7. 2005
  16. pmc Total synthesis and structural revision of vannusals A and B: synthesis of the originally assigned structure of vannusal B
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 132:7138-52. 2010
    ..These investigations led to the discovery and development of a number of new synthetic technologies that set the stage for the solution of the vannusal structural conundrum...
  17. ncbi request reprint The cytoskyrin cascade: a facile entry into cytoskyrin A, deoxyrubroskyrin, rugulin, skyrin, and flavoskyrin model systems
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:5846-51. 2005
  18. ncbi request reprint Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 45:2609-15. 2006
  19. ncbi request reprint Total synthesis of halipeptins A and D and analogues
    K C Nicolaou
    Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:4925-9. 2005
  20. pmc Total synthesis and structural revision of vannusals A and B: synthesis of the true structures of vannusals A and B
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 132:7153-76. 2010
    ....
  21. ncbi request reprint Palladium-catalyzed cross-coupling reactions in total synthesis
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:4442-89. 2005
    ..In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis...
  22. ncbi request reprint Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 127:11159-75. 2005
    ....
  23. doi request reprint Synthesis of functionalized maoecrystal V core structures
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block 03 08, Singapore
    Chem Commun (Camb) 46:70-2. 2010
    ..Two strategies toward the total synthesis of maoecrystal V (1) culminating in the construction of core structures 2 and 3 are described...
  24. pmc The continuing saga of the marine polyether biotoxins
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 47:7182-225. 2008
    ..The Review ends with a discussion of the, as yet unfinished, story of maitotoxin, and projects into the future of this area of research...
  25. doi request reprint An expedient asymmetric synthesis of platencin
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences ICES, Agency for Science, Technology and Research ASTAR, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 130:11292-3. 2008
    ..A short and efficient synthesis of enone 3, a key intermediate in the total synthesis of platencin (2), based on an intramolecular Diels-Alder reaction is described...
  26. pmc Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 130:11114-21. 2008
    ..Biological investigations with the synthesized biyouyangagins A (2-11) and hyperolactones C (12-16) revealed that the activity of biyouyanagin A most likely resides in its hyperolactone C structural domain...
  27. doi request reprint An expedient strategy for the synthesis of tryptamines and other heterocycles
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 47:4217-20. 2008
  28. pmc Total synthesis and absolute configuration of the bisanthraquinone antibiotic BE-43472B
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 48:3444-8. 2009
    ..Key transformations in the pivotal cascade sequence include a Diels-Alder reaction, a hemiketal formation, and a nucleophilic aromatic ipso substitution...
  29. doi request reprint Total synthesis of platencin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 47:1780-3. 2008
  30. ncbi request reprint Asymmetric synthesis and biological properties of uncialamycin and 26-epi-uncialamycin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 47:185-9. 2008
  31. ncbi request reprint Chemical synthesis of the GHIJK ring system and further experimental support for the originally assigned structure of maitotoxin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 46:8875-9. 2007
  32. ncbi request reprint Total synthesis of kinamycins C, F, and J
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 129:10356-7. 2007
  33. ncbi request reprint Asymmetric total syntheses of platensimycin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 46:3942-5. 2007
  34. ncbi request reprint Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 129:4001-13. 2007
    ..The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner...
  35. ncbi request reprint Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 129:1760-8. 2007
    ..Alternative direct dimerization approaches based on the Stille and Heck coupling reactions also led to monomarinomycins A (m-1 and m-2), but failed to deliver useful amounts of marinomycin A (1)...
  36. ncbi request reprint Cascade reactions in total synthesis
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 45:7134-86. 2006
    ..The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis...
  37. ncbi request reprint Total synthesis of marinomycins A-C
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 45:6527-32. 2006
  38. pmc Total synthesis of platensimycin and related natural products
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 131:16905-18. 2009
    ..The rhodium-catalyzed asymmetric reaction involving a terminal acetylene was developed as a general method for the asymmetric cycloisomerization of terminal enynes...
  39. doi request reprint Total synthesis of englerin A
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences ICES, Agency for Science, Technology and Research A STAR, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 132:8219-22. 2010
    ....
  40. ncbi request reprint Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:756-61. 2005
  41. ncbi request reprint Novel strategies to construct the gamma-hydroxy lactone moiety of the CP molecules. Synthesis of the CP-225,917 core skeleton
    K C Nicolaou
    Department of Chemistry, Scripps Research Institute, La Jolla, California, USA
    Org Lett 1:63-6. 1999
    ....
  42. pmc Synthesis and biological evaluation of 2',4'- and 3',4'-bridged nucleoside analogues
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Bioorg Med Chem 19:5648-69. 2011
    ..0 μM) and HxB2 (IC(50)=2.4 μM). These findings render bridged nucleosides as credible leads for drug discovery in the anti-HIV area of research...
  43. ncbi request reprint Atropselective macrocyclization of diaryl ether ring systems: application to the synthesis of vancomycin model systems
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 124:10451-5. 2002
    ..This reaction is used to synthesize the C-O-D diaryl ether macrocycle found in vancomycin with high diastereoselectivity (de > 90%), providing the naturally occurring atropisomeric configuration...
  44. ncbi request reprint New synthetic technology for the synthesis of hindered alpha-diazoketones via acyl mesylates
    K C Nicolaou
    Department of Chemistry, Scripps Research Institute, La Jolla, California 92037, USA
    Org Lett 1:883-6. 1999
    ....
  45. ncbi request reprint A new method for the synthesis of nonsymmetrical sulfamides using burgess-type reagents
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 41:3866-70. 2002
  46. ncbi request reprint Total synthesis of everninomicin 13,384-1--Part 3: synthesis of the DE fragment and completion of the total synthesis
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    Chemistry 6:3149-65. 2000
    ....
  47. ncbi request reprint The CP molecule labyrinth: a paradigm of how endeavors in total synthesis lead to discoveries and inventions in organic synthesis
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 41:2678-720. 2002
    ....
  48. ncbi request reprint Total synthesis of everninomicin 13,384-1--Part 4: explorations of methodology; stereocontrolled synthesis of 1,1'-disaccharides, 1,2-seleno migrations in carbohydrates, and solution- and solid-phase synthesis of 2-deoxy glycosides and orthoesters
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    Chemistry 6:3166-85. 2000
    ..The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals...
  49. ncbi request reprint Chemical synthesis and biological properties of pyridine epothilones
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA
    Chem Biol 7:593-9. 2000
    ....
  50. ncbi request reprint Novel chemistry of alpha-tosyloxy ketones: applications to the solution- and solid-phase synthesis of privileged heterocycle and enediyne libraries
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 124:5718-28. 2002
    ..The accessibility and site-selectivity of the chemistry demonstrated herein offer the promise of an expanded use for this moiety in solid-phase library construction, in particular, and in the field of organic synthesis, in general...
  51. pmc Synthesis of the ABCDEFG ring system of maitotoxin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 132:6855-61. 2010
    ....
  52. pmc From nature to the laboratory and into the clinic
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, BCC408, La Jolla, CA 92037, USA
    Bioorg Med Chem 17:2290-303. 2009
    ..e., dynemicin A (8), uncialamycin (9), eleutherobin (10), sarcodictyin A (11), azaspiracid-1 (12), thiostrepton (13), abyssomicin C (14), platensimycin (15), platencin (16), and palmerolide A (17)]...
  53. ncbi request reprint Total synthesis of the proposed azaspiracid-1 structure, part 2: coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion of the synthesis
    K C Nicolaou
    Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 42:3649-53. 2003
  54. ncbi request reprint New reactions of IBX: oxidation of nitrogen- and sulfur-containing substrates to afford useful synthetic intermediates
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 42:4077-82. 2003
  55. ncbi request reprint Novel strategies for the solid phase synthesis of substituted indolines and indoles
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550North Torrey Pines Road, La Jolla, CA 92037, USA
    Bioorg Med Chem 11:465-76. 2003
    ....
  56. ncbi request reprint New uses for the Burgess reagent in chemical synthesis: methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Chemistry 10:5581-606. 2004
    ..Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further...
  57. ncbi request reprint Chemistry and biology of diazonamide A: second total synthesis and biological investigations
    K C Nicolaou
    Contribution from the Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 126:12897-906. 2004
    ..We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl(3)...
  58. ncbi request reprint Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Angew Chem Int Ed Engl 43:5087-92. 2004
  59. ncbi request reprint Structural revision and total synthesis of azaspiracid-1, part 1: intelligence gathering and tentative proposal
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 43:4312-8. 2004
  60. ncbi request reprint Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 126:10162-73. 2004
    ....
  61. pmc The essence of total synthesis
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Proc Natl Acad Sci U S A 101:11929-36. 2004
    ..This perspective article seeks to examine this time-honored and highly demanding art, distilling its essence in an effort to ascertain its power and future potential...
  62. ncbi request reprint o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093 USA
    J Am Chem Soc 126:5192-201. 2004
    ..Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways...
  63. pmc Design, synthesis, and biological evaluation of a biyouyanagin compound library
    K C Nicolaou
    Department of Chemistry, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Proc Natl Acad Sci U S A 108:6715-20. 2011
    ....
  64. ncbi request reprint Total synthesis of hybocarpone and analogues thereof. A facile dimerization of naphthazarins to pentacyclic systems
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 126:607-12. 2004
    ....
  65. ncbi request reprint Total synthesis and biological evaluation of (-)apicularen A and analogues thereof
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Chemistry 9:6177-91. 2003
    ....
  66. pmc Total synthesis of epicoccin G
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    J Am Chem Soc 133:8150-3. 2011
    ..An expedient enantioselective total synthesis of epicoccin G and related dithiodiketopiperazines through a strategy featuring direct two-directional sulfenylation, photooxygenation, and Kornblum-DeLaMare rearrangement is described...
  67. ncbi request reprint Total synthesis of apoptolidin: construction of enantiomerically pure fragments
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 125:15433-42. 2003
    ..First and second generation syntheses to the required fragments for apoptolidin (1) are described...
  68. ncbi request reprint Combinatorial synthesis through disulfide exchange: discovery of potent psammaplin A type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA)
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    Chemistry 7:4280-95. 2001
    ..The present, catalytically-induced, disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries...
  69. ncbi request reprint Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria: target-accelerated combinatorial synthesis
    K C Nicolaou
    Department of Chemistry, and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla 92037, USA
    Chemistry 7:3824-43. 2001
    ..Screening of these compound libraries led to the identification of a number of highly potent antibiotics effective against vancomycin-suspectible, vancomycin-intermediate resistant and, most significantly, vancomycin-resistant bacteria...
  70. ncbi request reprint Optimization and mechanistic studies of psammaplin A type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA)
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA
    Chemistry 7:4296-310. 2001
    ..Evaluation of the selectivity and serum binding properties of some of the most promising compounds and preliminary studies directed at deciphering the mechanism of action of this novel class of antibacterial agents are also included...
  71. ncbi request reprint Total synthesis of abyssomicin C, atrop-abyssomicin C, and abyssomicin D: implications for natural origins of atrop-abyssomicin C
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 129:429-40. 2007
    ..Finally, to gain insight into the mechanism of antiobiotic activity, several synthetic intermediates and designed analogues were evaluated for biological activity...
  72. pmc Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B
    Amy E Hayden
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E Young Drive, Los Angeles, California 90095 1569, USA
    J Org Chem 75:922-8. 2010
    ..In this article, the effect of an aromatic conjugating group bonded to juglone is explored...
  73. ncbi request reprint Iodine(V) reagents in organic synthesis. Part 2. Access to complex molecular architectures via Dess-Martin periodinane-generated o-imidoquinones
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 124:2221-32. 2002
    ..Among its most useful reactions is a set of cascade heterocyclic annulations leading to a variety of polycyclic systems of possible biological relevance...
  74. ncbi request reprint Chemical synthesis and biological evaluation of cis- and trans-12,13-cyclopropyl and 12,13-cyclobutyl epothilones and related pyridine side chain analogues
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 123:9313-23. 2001
    ..These studies also confirmed the importance of both the cyclopropyl and 5-methylpyridine moieties in conferring potent and potentially clinically useful biological properties to the epothilone scaffold...
  75. doi request reprint Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 131:2086-7. 2009
    ....
  76. ncbi request reprint Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone
    Amy E Hayden
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 8:2989-92. 2006
    ....
  77. ncbi request reprint Adamantaplatensimycin: a bioactive analogue of platensimycin
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 46:4712-4. 2007
  78. doi request reprint Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 47:1432-5. 2008
  79. pmc Inspirations, discoveries, and future perspectives in total synthesis
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Org Chem 74:951-72. 2009
    ..Indeed, the advent of chemical synthesis as a whole must be considered as one of the most influential developments of the twentieth century in terms of its impact on society...
  80. ncbi request reprint Stereocontrolled total synthesis of apicularen A and its delta(17,18) Z isomer
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 41:3701-4; 3523. 2002
  81. pmc The art of total synthesis through cascade reactions
    K C Nicolaou
    The Scripps Research Institute, Department of Chemistry, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Chem Soc Rev 38:2993-3009. 2009
    ..In this tutorial review, we highlight the design and execution of cascade reactions within the context of total synthesis as demonstrated with selected examples from these laboratories...
  82. doi request reprint Total synthesis and biological evaluation of cortistatins A and J and analogues thereof
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences ICES, Agency for Science, Technology and Research ASTAR, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 131:10587-97. 2009
    ....
  83. doi request reprint Total synthesis of hopeahainol A and hopeanol
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667, Singapore
    Angew Chem Int Ed Engl 48:3440-3. 2009
    ..Their first total synthesis has now been achieved through a series of novel cascade reactions and skeletal rearrangements...
  84. pmc Samarium diiodide mediated reactions in total synthesis
    K C Nicolaou
    Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 48:7140-65. 2009
    ..The examples discussed are both illustrative of the power of this reagent in the construction of complex molecules and inspirational for the design of synthetic strategies toward such targets, both natural and designed...
  85. ncbi request reprint Synthesis and biological properties of C12,13-cyclopropyl-epothilone A and related epothilones
    K C Nicolaou
    Department of Chemistry The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Chem Biol 5:365-72. 1998
    ..The development of detailed structure-activity relationships for these compounds and the further elucidation of their mechanism of action is of high priority...
  86. pmc Total synthesis of sporolide B
    K C Nicolaou
    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 48:3449-53. 2009
    ..The key steps involve a ruthenium-catalyzed [2+2+2] cycloaddition to assemble the indene structural motif and a thermally induced Diels-Alder-type reaction to forge the macrocycle (see scheme)...
  87. doi request reprint Total synthesis of (+)-cortistatin A
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences, Agency for Science, Technology, and Research, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667, Singapore
    Angew Chem Int Ed Engl 47:7310-3. 2008
  88. ncbi request reprint Metathesis reactions in total synthesis
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:4490-527. 2005
    ..Judging from their short but impressive history, the influence of these reactions in chemical synthesis is destined to increase...
  89. ncbi request reprint Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:1012-44. 2005
    ....
  90. ncbi request reprint A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 44:1378-82. 2005
  91. ncbi request reprint Total synthesis of hamigerans and analogues thereof. Photochemical generation and Diels-Alder trapping of hydroxy-o-quinodimethanes
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    J Am Chem Soc 126:613-27. 2004
    ..A number of analogues of these biologically active natural products were also prepared by application of the developed technology...
  92. ncbi request reprint Total synthesis of apoptolidin: completion of the synthesis and analogue synthesis and evaluation
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 125:15443-54. 2003
    ..The developed synthetic technology was applied to the construction of several analogues including 74, 75, and 77 which exhibit significant bioactivity against tumor cells...
  93. ncbi request reprint Studies towards the synthesis of azadirachtin: enantioselective entry into the azadirachtin framework through cascade reactions
    K C Nicolaou
    Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 42:3637-42. 2003
  94. ncbi request reprint Total synthesis of diazonamide A
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA
    Angew Chem Int Ed Engl 41:3495-9. 2002
  95. ncbi request reprint Solid phase synthesis of complex natural products and libraries thereof
    K C Nicolaou
    Department of Chemistry, and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    Biopolymers 60:171-93. 2001
    ..Issues such as target selection, library design, linker development, automation, and library characterization are addressed...
  96. ncbi request reprint Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    Chemistry 6:3116-48. 2000
    ..Final success for the latter construction came when a novel 1,2-phenylseleno migration reaction was applied to couple rings G and H, followed by ketene acetal and orthoester formation...
  97. ncbi request reprint Total synthesis and structural elucidation of azaspiracid-1. Construction of key building blocks for originally proposed structure
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
    J Am Chem Soc 128:2244-57. 2006
    ....
  98. ncbi request reprint Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues
    K C Nicolaou
    Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA
    Chemistry 6:2783-800. 2000
    ....
  99. ncbi request reprint Construction of highly functionalized medium-sized rings: synthesis of hyperforin and perforatumone model systems
    K C Nicolaou
    Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
    Angew Chem Int Ed Engl 44:3895-9. 2005
  100. doi request reprint Total synthesis of the originally proposed and revised structures of palmerolide A and isomers thereof
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, 03 08, Singapore 138667
    J Am Chem Soc 130:3633-44. 2008
    ..The syntheses were completed by attachment of the enamide moiety through a copper-catalyzed coupling process...
  101. doi request reprint A chiral pool based synthesis of platensimycin
    K C Nicolaou
    Chemical Synthesis Institute of Chemical and Engineering Sciences ICES, Agency for Science, Technology and Research A STAR, 11 Biopolis Way, The Helios Block, No 03 08, Singapore 138667, Singapore
    Angew Chem Int Ed Engl 47:944-6. 2008

Research Grants37

  1. TOTAL SYNTHESIS OF AZASPIRACIDS
    K Nicolaou; Fiscal Year: 2006
    ..g. lung, liver, spleen and lymphocyte damage as well as cancer) health hazards. The project is also expected to advance our knowledge in chemical synthesis and impact favorably the drug discovery and development process. ..
  2. TOTAL SYNTHESIS OF AZADIRACHTIN
    K Nicolaou; Fiscal Year: 2007
    ..The proposed work is expected to impact the general areas of pharmaceutical and agricultural research, and infectious diseases in particular, through discoveries in synthetic organic chemistry and chemical biology. ..
  3. SYNTHESIS OF ANTIBIOTICS
    K Nicolaou; Fiscal Year: 2007
    ....
  4. TOTAL SYNTHESIS OF KINAMYCINS AND LOMAIVITICINS
    K Nicolaou; Fiscal Year: 2007
    ..The significance of the proposed work will lie specifically in the area of cancer chemotherapy research, and in the development of new synthetic strategies and technologies for general use in the drug discovery and development process. ..
  5. Synthesis of Marine Neurotoxins
    K Nicolaou; Fiscal Year: 2007
    ..The project is also expected to significantly advance our knowledge in chemical synthesis, chemical biology, and medicine ..
  6. SYNTHESIS OF ANTICANCER AGENTS
    K C Nicolaou; Fiscal Year: 2010
    ..abstract_text> ..
  7. SYNTHESIS OF ANTIBIOTICS
    K C Nicolaou; Fiscal Year: 2010
    ..abstract_text> ..
  8. TOTAL SYNTHESIS OF THIOSTREPTON
    K Nicolaou; Fiscal Year: 2005
    ..The disease areas likely to benefit most from the proposed investigations are bacterial-caused diseases and malaria. ..
  9. TOTAL SYNTHESIS OF NATURAL PRODUCTS
    K Nicolaou; Fiscal Year: 2002
    ..3] sigmatropic rearrangement and a radical based ring closure to form the bicyclic skeleton. ..
  10. TOTAL SYNTHESIS OF APOPTOLIDIN
    K Nicolaou; Fiscal Year: 2004
    ..The proposed work is expected to have significant impact in the area of cancer chemotherapy and should provide enabling technologies and tools for biology and medicine. ..
  11. Enabling Technologies for Combinatorial Chemistry
    K Nicolaou; Fiscal Year: 2005
    ..abstract_text> ..
  12. Synthesis of Marine Neurotoxins
    K C Nicolaou; Fiscal Year: 2010
    ..The project is also expected to significantly advance our knowledge in chemical synthesis, chemical biology, and medicine ..