BARRY TROST

Summary

Affiliation: Stanford University
Country: USA

Publications

  1. doi request reprint Palladium-catalyzed ch activation of N-allyl imines: regioselective allylic alkylations to deliver substituted aza-1,3-dienes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5580 USA
    Angew Chem Int Ed Engl 54:6032-6. 2015
  2. doi request reprint Development of chiral sulfoxide ligands for asymmetric catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA
    Angew Chem Int Ed Engl 54:5026-43. 2015
  3. pmc Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:3931-3. 2006
  4. pmc Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:6314-5. 2006
  5. pmc Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    J Am Chem Soc 128:2540-1. 2006
  6. pmc Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford University, CA 94305 5080, USA
    Chemistry 17:2916-22. 2011
  7. ncbi request reprint Ruthenium-catalyzed reactions--a treasure trove of atom-economic transformations
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 44:6630-66. 2005
  8. ncbi request reprint Development of aliphatic alcohols as nucleophiles for palladium-catalyzed DYKAT reactions: total synthesis of (+)-hippospongic acid A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    J Am Chem Soc 127:7014-24. 2005
  9. ncbi request reprint Ruthenium-catalyzed cycloisomerizations of diynols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    J Am Chem Soc 127:4763-76. 2005
  10. pmc Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:1474-7. 2012

Research Grants

Detail Information

Publications223 found, 100 shown here

  1. doi request reprint Palladium-catalyzed ch activation of N-allyl imines: regioselective allylic alkylations to deliver substituted aza-1,3-dienes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5580 USA
    Angew Chem Int Ed Engl 54:6032-6. 2015
    ..In contrast, nucleophilic attack by the α-aryl cyanoester exclusively delivered the 2-aza-1,3-diene, which was employed in an inverse-electron-demand Diels-Alder reaction for heterobiaryl synthesis. ..
  2. doi request reprint Development of chiral sulfoxide ligands for asymmetric catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA
    Angew Chem Int Ed Engl 54:5026-43. 2015
    ..We also provide brief descriptions of metal-sulfoxide bonding and strategies for the synthesis of enantiopure sulfoxides. Finally, insights into the future development of this underutilized ligand class are discussed. ..
  3. pmc Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:3931-3. 2006
    ..The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature...
  4. pmc Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:6314-5. 2006
    ..A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine...
  5. pmc Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    J Am Chem Soc 128:2540-1. 2006
    ..Highly efficient kinetic resolution is also possible using this methodology...
  6. pmc Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford University, CA 94305 5080, USA
    Chemistry 17:2916-22. 2011
    ..Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported...
  7. ncbi request reprint Ruthenium-catalyzed reactions--a treasure trove of atom-economic transformations
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 44:6630-66. 2005
    ..These complexes often exhibit unusual reactivity. Careful consideration of the mechanistic underpinnings of the transformations can lead to the design of new reactions and the discovery of new reactivity...
  8. ncbi request reprint Development of aliphatic alcohols as nucleophiles for palladium-catalyzed DYKAT reactions: total synthesis of (+)-hippospongic acid A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    J Am Chem Soc 127:7014-24. 2005
    ..The synthesis features three palladium-catalyzed allylic alkylation reactions to introduce three different bond types: C-S, C-H, and C-O...
  9. ncbi request reprint Ruthenium-catalyzed cycloisomerizations of diynols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    J Am Chem Soc 127:4763-76. 2005
    ..Primary diynols undergo a cycloisomerization as well as a hydrative cyclization process. The utility of primary diynol cycloisomerization is demonstrated in a synthesis of (+)-alpha-kainic acid...
  10. pmc Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:1474-7. 2012
    ....
  11. doi request reprint A concise synthesis of (-)-oseltamivir
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    Angew Chem Int Ed Engl 47:3759-61. 2008
  12. ncbi request reprint Asymmetric annulation toward pyrrolopiperazinones: concise enantioselective syntheses of pyrrole alkaloid natural products
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 9:2357-9. 2007
    ..In this paper, the total synthesis of (-)-longamide B in five steps and the first total syntheses of agesamides A and B in six steps from 6 and 7 are reported...
  13. pmc Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols
    Barry M Trost
    Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:2075-84. 2012
    ....
  14. doi request reprint Readily accessible chiral diene ligands for Rh-catalyzed enantioselective conjugate additions of boronic acids
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 13:4566-9. 2011
    ..Subsequently, these ligands were evaluated in the Rh-catalyzed asymmetric conjugate addition of boronic acids to enones...
  15. ncbi request reprint Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool
    Barry M Trost
    Department of Chemistry, Stanford University, CA 94305 5080, USA
    Chem Pharm Bull (Tokyo) 50:1-14. 2002
    ....
  16. ncbi request reprint Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl aziridines with imido carboxylates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    Angew Chem Int Ed Engl 46:6123-5. 2007
  17. doi request reprint Palladium-catalyzed asymmetric benzylation of azlactones
    Barry M Trost
    Department of Chemistry, Stanford University, 337 Campus Drive Stanford, CA 94305 USA
    Chemistry 19:15210-8. 2013
    ..The high levels of asymmetric induction, as well as the reactivity pattern of the electrophiles, suggest an η(3)-benzyl intermediate that arises through two distinct pathways...
  18. ncbi request reprint Ruthenium-catalyzed alkylative lactonization and carbocyclization
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    Org Lett 8:3627-9. 2006
    ..The mild reaction conditions allow for the presence of various functional groups...
  19. ncbi request reprint Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:12565-79. 2004
    ..These studies may shed light on the biosynthesis of this novel family of compounds...
  20. pmc Development of a flexible strategy towards FR900482 and the mitomycins
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 17:7890-903. 2011
    ....
  21. pmc Total synthesis of bryostatins: the development of methodology for the atom-economic and stereoselective synthesis of the ring C subunit
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 17:9762-76. 2011
    ..Elaboration of this methodology ultimately led to a concise synthesis of the ring C subunit of bryostatins...
  22. ncbi request reprint Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Am Chem Soc 127:14785-803. 2005
    ..The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine...
  23. pmc Asymmetric stereodivergent strategy towards aminocyclitols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA USA
    Chemistry 20:8288-92. 2014
    ..These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α-glucosidase inhibitors...
  24. pmc Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 132:8915-7. 2010
    ..The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil...
  25. ncbi request reprint Asymmetric allylic alkylation, an enabling methodology
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Org Chem 69:5813-37. 2004
    ..novel synthetic strategies emerge that provide short efficient asymmetric syntheses...
  26. pmc Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:17823-31. 2012
    ..The remote stereoinduction afforded by the catalyst, distal from the chiral pocket generated by the ligand, is proposed to be the result of a new mechanism invoking the Curtin-Hammett principle...
  27. ncbi request reprint A highly enantio- and diastereoselective molybdenum-catalyzed asymmetric allylic alkylation of cyanoesters
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 133:8165-7. 2011
    ..This method generates a number of functionalized cyanoesters in excellent yield and chemoselectivity in good to excellent diastereoselectivity and enantioselectivity...
  28. pmc Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:17644-55. 2005
    ..This advantage is demonstrated in the direct synthesis of triene substrates for silicon-tethered intramolecular Diels-Alder cycloadditions...
  29. ncbi request reprint A diosphenol-based strategy for the total synthesis of (-)-terpestacin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 129:4540-1. 2007
  30. pmc Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:14548-9. 2007
    ..A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed...
  31. pmc Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 131:18343-57. 2009
    ..The much milder reaction conditions as well as the much broader substrate scope also represent the advantages of the DAAA reaction over the direct allylation of preformed metal enolates...
  32. ncbi request reprint Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: application to the formal total synthesis of (-)-physostigmine
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:4590-1. 2006
    ..A variety of 3-alkyl oxindoles can be alkylated with high yields and enantioselectivity. This method provides expedited access to (-)-physostigmine and its analogues...
  33. ncbi request reprint Syntheses of seven-membered rings: ruthenium-catalyzed intramolecular [5+2] cycloadditions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 11:2577-90. 2005
    ..The potential power of this methodology towards natural product total synthesis is demonstrated by the formation of several polycyclic systems with the chosen reaction conditions and readily available cyclopropylenyne substrates...
  34. pmc Exploiting the Pd- and Ru-catalyzed cycloisomerizations: enantioselective total synthesis of (+)-allocyathin B2
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94301 5080, USA
    J Am Chem Soc 127:10259-68. 2005
    ..Mechanistic rationalization is proposed for these observations...
  35. doi request reprint Enantioselective construction of highly substituted vinylidenecylopentanes by palladium-catalyzed asymmetric [3+2] cycloaddition reaction
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 52:6262-4. 2013
    ..An asymmetric protocol using this unique donor forms cycloadducts in excellent yield and enantioselectivity, making use of a bisdiamidophosphite ligand derived from trans-1,2-stilbenediamine...
  36. pmc Atom-economic and stereoselective syntheses of the ring a and B subunits of the bryostatins
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 17:9777-88. 2011
    ..Utilization of these methods ultimately led to the rapid assembly of the northern bryostatin fragment containing both the ring A and B subunits...
  37. pmc Differential reactivities of enyne substrates in ruthenium- and palladium-catalyzed cycloisomerizations
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Am Chem Soc 132:9206-18. 2010
    ....
  38. pmc Selective synthesis of functionalized, tertiary silanes by diastereoselective rearrangement-addition
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    Org Lett 7:4911-3. 2005
    ..In addition to providing functionalized tertiary silane products, the method is shown to offer a tertiary olefin synthesis through chemo- and diastereoselective Peterson elimination of the product tertiary silane diols...
  39. pmc Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol
    Barry M Trost
    Department of Chemistry, University of Stanford, Stanford, CA 94035 5080 USA
    Angew Chem Int Ed Engl 51:6704-8. 2012
    ..The resulting products are attractive synthons which are produced with good to excellent enantiocontrol, and show broad tolerance and applicability, as demonstrated by the synthesis (+)-tetrahydropyrenophorol...
  40. pmc Ligand controlled highly regio- and enantioselective synthesis of alpha-acyloxyketones by palladium-catalyzed allylic alkylation of 1,2-enediol carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:11852-3. 2008
    ..Besides the commonly used protection groups such as OAc and OPiv, a more functionalized group such as methyl but-2-enoyl group can also be used, downstream process of which can afford other synthetically interesting structures...
  41. pmc A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 15:6910-9. 2009
    ..A unique feature of our syntheses is the use of two rather different strategies for the total syntheses of both enantiomers of agelastatin A using the same enantiomer of a chiral palladium catalyst...
  42. ncbi request reprint Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+2] cycloaddition
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:11781-90. 2007
    ..This is the first application of a Ru-catalyzed [5+2] cycloaddition in the total synthesis of a natural product. Through this synthesis, the absolute configuration of (+)-frondosin A was established...
  43. doi request reprint Palladium-catalyzed alkylation of 1,4-dienes by C-H activation
    Barry M Trost
    Department of Chemistry, Stanford University, CA 94305 5080, USA
    Angew Chem Int Ed Engl 51:4950-3. 2012
    ..This is the first catalytic allylic C-H alkylation that proceeds in the absence of sulfoxide ligands...
  44. ncbi request reprint Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:11966-83. 2004
    ....
  45. ncbi request reprint An alkyne strategy for the asymmetric synthesis of natural products: application to (+)-spirolaxine methyl ether
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 46:7664-6. 2007
  46. ncbi request reprint Catalytic enantioselective synthesis of adociacetylene B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 8:4461-4. 2006
    ..A catalytic enantioselective total synthesis of adociacetylene B (2) in five steps is reported. The efficiency of this synthesis was enabled by an asymmetric zinc alkynylation catalyzed by the proline-derived ligand (1)...
  47. pmc Development of an asymmetric trimethylenemethane cycloaddition reaction: application in the enantioselective synthesis of highly substituted carbocycles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 133:19483-97. 2011
    ..These donors were reactive with unsaturated acylpyrroles, giving the product cyclopentane rings bearing three stereocenters in high enantioselectivity and complete diastereoselectivity...
  48. pmc Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:1322-5. 2012
    ....
  49. ncbi request reprint A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:861-3. 2002
  50. ncbi request reprint Intramolecular endo-dig hydrosilylation catalyzed by ruthenium: evidence for a new mechanistic pathway
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 125:30-1. 2003
    ..However, the evidence for any products of syn addition with nonhydrido ruthenium catalysts is very scarce. Alternatively, a direct trans addition to orthogonal p-systems is also a possibility...
  51. ncbi request reprint Vanadium-catalyzed anti-selective additions of allenols to imines
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 42:2063-6. 2003
  52. ncbi request reprint A direct catalytic asymmetric mannich-type reaction to syn-amino alcohols
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    J Am Chem Soc 125:338-9. 2003
    ..In this communication, we report the application of our dinuclear zinc catalyst to a highly asymmetric Mannich-type reaction to generate syn 1,2-amino alcohols...
  53. pmc Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 18:16498-509. 2012
    ..The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products...
  54. pmc The O-acylation of ketone enolates by allyl 1H-imidazole-1-carboxylate mediated with boron trifluoride etherate: a convenient procedure for the synthesis of substituted allyl enol carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Org Chem 72:9372-5. 2007
    ..A convenient access to substituted allyl enol carbonates was established through the reaction of ketone enolates with the complex of allyl 1H-imidazole-1-carboxylates and boron trifluoride etherate...
  55. ncbi request reprint Development of diamidophosphite ligands and their application to the palladium-catalyzed vinyl-substituted trimethylenemethane asymmetric [3 + 2] cycloaddition
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:11319-21. 2012
    ..This transformation generates tetrasubstituted cyclopentanes bearing three contiguous stereocenters in high yields, with good diastereo- and enantioselectivity...
  56. ncbi request reprint Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: synthesis of 3-allyl-3-aryl oxindoles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 44:308-10. 2004
  57. pmc Dinuclear zinc-ProPhenol-catalyzed enantioselective α-hydroxyacetate aldol reaction with activated ester equivalents
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 15:4516-9. 2013
    ..The resulting α,β-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones. ..
  58. ncbi request reprint Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    Org Lett 4:2621-3. 2002
    ..Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the beta-receptor agonists (-)-denopamine and (-)-arbutamine...
  59. ncbi request reprint Contemporaneous dual catalysis by coupling highly transient nucleophilic and electrophilic intermediates generated in situ
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, United States
    J Am Chem Soc 133:1706-9. 2011
    ..Notably, this dual catalysis is achieved using low catalyst loadings (1.0 mol % [Pd], 1.5 mol % [V]) and gives good to excellent yields (up to 98%) of the desired products...
  60. ncbi request reprint Concise total synthesis of (+/-)-marcfortine B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:3086-7. 2007
  61. ncbi request reprint Enantioselective Synthesis of Tertiary α-Hydroxyketones from Unfunctionalized Ketones: Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 51:8290-3. 2012
    ..Highly functionalized tertiary α-hydroxyketones can be obtained in high yield with excellent enantioselectivity using this method...
  62. ncbi request reprint Total syntheses of furaquinocin A, B, and E
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 125:13155-64. 2003
    ..The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B...
  63. ncbi request reprint Contemporaneous dual catalysis: chemoselective cross-coupling of catalytic vanadium-allenoate and π-allylpalladium intermediates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, United States
    J Am Chem Soc 133:12824-33. 2011
    ....
  64. ncbi request reprint Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Acc Chem Res 39:747-60. 2006
    ..This Account highlights the mechanistic aspects considered when designing reactions with DPPBA-based ligands and presents a working model for the a priori prediction of their stereochemical outcome...
  65. pmc Palladium-catalyzed asymmetric allylic alpha-alkylation of acyclic ketones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:17180-1. 2005
    ..An alternative mechanism was proposed, which involves an inner sphere process of coordination of the enolate to Pd followed by reductive elimination...
  66. pmc Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305, USA
    Chemistry 16:296-303. 2010
    ..Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis...
  67. pmc A concise enantioselective synthesis of (-)-ranirestat
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    Org Lett 12:1276-9. 2010
    ..A palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) of malonate 4 was utilized as a key transformation to construct the tetrasubstituted chiral center in the target...
  68. ncbi request reprint Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 12:6607-20. 2006
    ..In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration...
  69. pmc Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 131:4190-1. 2009
    ..Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction...
  70. pmc Sequential Ru-Pd catalysis: a two-catalyst one-pot protocol for the synthesis of N- and O-heterocycles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Am Chem Soc 128:6745-54. 2006
    ..Finally, the utility of these heterocyclic products in total synthesis is demonstrated through concise syntheses of a kainoid intermediate, a constituent of oil of rose, and the ring B portion of bryostatin, a potent chemotherapeutic...
  71. pmc Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:8602-3. 2005
    ..For example, convergent fragment coupling methods have been demonstrated via highly diastereoselective cycloaddition of nitrile oxide after reduction into 1,3-diol or via cross-metathesis reaction...
  72. ncbi request reprint Palladium-catalyzed regio- and enantioselective allylic alkylation of bis allylic carbonates derived from Morita-Baylis-Hillman adducts
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    Org Lett 9:3961-4. 2007
    ..Morita-Baylis-Hillman diene adducts are used as substrates in the palladium-catalyzed asymmetric allylic alkylation reaction with oxygen and carbon nucleophiles in good regio- and enantioselectivity...
  73. ncbi request reprint Synthesis of substituted 1,3-diene synthetic equivalents by a Ru-catalyzed diyne hydrative cyclization
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chem Asian J 1:469-78. 2006
    ..The utility of this method was demonstrated by both sulfur dioxide extrusion of the 3-sulfolenes to afford 1,3-dienes and subsequent inter- or intramolecular Diels-Alder reactions...
  74. pmc Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:17258-9. 2008
    ....
  75. pmc Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Nature 456:485-8. 2008
    ..Analogues of bryostatin that do not exist in nature could be readily made by following this route, which might allow the biological activity of bryostatins to be fine-tuned...
  76. pmc Exploiting orthogonally reactive functionality: synthesis and stereochemical assignment of (-)-ushikulide A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:16190-2. 2008
    ..This approach has the dual effect of minimizing the number of steps and protecting groups required for our synthetic route. This strategy culminated in the efficient synthesis and stereochemical assignment of ushikulide A...
  77. ncbi request reprint Total synthesis of (+)-amphidinolide A. Assembly of the fragments
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:13589-97. 2005
    ..Diastereomers of 6 and 7 were easily prepared by modification of the synthetic routes to allow access to multiple diastereomers of 1 for structural determination...
  78. ncbi request reprint Dinuclear asymmetric Zn aldol additions: formal asymmetric synthesis of fostriecin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California, 94305 5080, USA
    J Am Chem Soc 127:3666-7. 2005
    ..5% overall yield...
  79. ncbi request reprint Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 4:2005-8. 2002
    ..Chemoselective allylation of (bis)indole lactam pro-aglycon 3 allows access to N-distally substituted indolopyrrolocarbazole derivatives; glyoxamide precursor 14 provides entry into N-proximally substituted derivatives...
  80. ncbi request reprint Ruthenium-catalyzed alkyne-propargyl alcohol addition. An asymmetric total synthesis of (+)-alpha-kainic acid
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Org Lett 5:1467-70. 2003
    ..A single stereocenter introduced by an asymmetric reduction of a ketone sets the stage for all the other stereocenters. A novel 1,6-addition of silyl cuprate serves to install a hydroxyl group at the diene termines. [reaction: see text]..
  81. ncbi request reprint A formal synthesis of (-)-mycalamide A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:48-9. 2004
    ..The first one is chemoselective, while the second one is highly diastereoselective. Three additional steps would be required to complete a total synthesis of (-)-mycalamide A...
  82. ncbi request reprint Migratory hydroamination: a facile enantioselective synthesis of benzomorphans
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 125:8744-5. 2003
    ..The strategy outlined here for the enantioselective synthesis of three contiguous stereogenic centers and the novel cycloisomerization should have many applications in alkaloid synthesis...
  83. ncbi request reprint Enantioselective synthesis of (-)-codeine and (-)-morphine
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 124:14542-3. 2002
    ..The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine...
  84. ncbi request reprint Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 125:2410-1. 2003
    ..A model to rationalize the results is presented...
  85. ncbi request reprint Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    Org Lett 5:1895-8. 2003
    ..The BDMS-vinylsilanes are further elaborated through mild palladium-catalyzed cross coupling and show significant stability to intervening synthetic operations, including silyl ether deprotection...
  86. ncbi request reprint A flexible approach toward trans-fused polycyclic tetrahydropyrans. A synthesis of prymnesin and yessotoxin units
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 6:4311-3. 2004
    ..Ru-catalyzed cycloisomerization and oxidative cyclization of bis-homopropargylic alcohols provide a rapid iterative approach to structural units of the ladder toxins...
  87. pmc Palladium-catalyzed allylic alkylation of carboxylic Acid derivatives: N-acyloxazolinones as ester enolate equivalents
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 51:204-8. 2012
    ..The imide products were readily converted into a series of carboxylic acid derivatives without loss of enantiopurity...
  88. ncbi request reprint 4-Aryloxybutenolides as "chiral aldehyde" equivalents: an efficient enantioselective synthesis of (+)-brefeldin a
    Barry M Trost
    Department of Chemistry, Stanford University, California 94305 5080, USA
    J Am Chem Soc 124:9328-9. 2002
    ..This synthesis also highlights the Pd-catalyzed DYKAT of crotyl carbonate to create the remote stereocenter. A new two-step method to convert aldehydes to delta-hydroxy-E-alpha,beta-enoates is also outlined...
  89. pmc Total synthesis of laulimalide: assembly of the fragments and completion of the synthesis of the natural product and a potent analogue
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 18:2961-71. 2012
    ..We also report a second generation route that provides a more concise synthesis of the natural product...
  90. ncbi request reprint Highly stereoselective synthesis of α-alkyl-α-hydroxycarboxylic acid derivatives catalyzed by a dinuclear zinc complex
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 51:6480-3. 2012
    ..This work highlights the utility of the ProPhenol family of ligands. The modular nature of these ligands proved crucial in the optimization of reaction conditions to achieve excellent stereoselectivities...
  91. ncbi request reprint Synthesis of novel quaternary amino acids using molybdenum-catalyzed asymmetric allylic alkylation
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 124:7256-7. 2002
    ..The reactions complements the Pd AAA wherein the cinnamyl substrate leads to only the product of attack at the primary terminus of the allyl moiety...
  92. ncbi request reprint Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 125:4518-26. 2003
    ..A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results...
  93. pmc Enantioselective synthesis of 2,2-disubstituted tetrahydrofurans: palladium-catalyzed [3+2] cycloadditions of trimethylenemethane with ketones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080 USA
    Angew Chem Int Ed Engl 52:4466-9. 2013
    ..The reaction is catalyzed by palladium in the presence of L1, which possesses a stereogenic phosphorus atom, and only a single epimer at the phosphorus atom yields the active catalyst. Cp=cyclopentadiene, TMS=trimethylsilyl...
  94. ncbi request reprint An enantioselective biomimetic total synthesis of (-)-siccanin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 42:3943-7. 2003
  95. ncbi request reprint Palladium-catalyzed DYKAT of vinyl epoxides: enantioselective total synthesis and assignment of the configuration of (+)-Broussonetine G
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 42:5987-90. 2003
  96. doi request reprint Tandem Palladium(0) and Palladium(II)-Catalyzed Allylic Alkylation Through Complementary Redox Cycles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 51:11522-6. 2012
    ..This allows for the selective introduction of otherwise indistinguishable allyl groups...
  97. doi request reprint Exploring the unique reactivity of diazoesters: an efficient approach to chiral β-amino acids
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 15:440-3. 2013
    ..This transformation enables access to optically enriched β-amido-α-diazoesters. These products are transformed to β-amino acids not readily accessible using known methods...
  98. pmc Palladium-catalyzed regio-, diastereo-, and enantioselective benzylic allylation of 2-substituted pyridines
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 131:12056-7. 2009
    ....
  99. pmc Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 131:17087-9. 2009
    ..The designed synthetic route also allowed us to prepare an analogue of the natural product that possesses significant cytotoxic activity...
  100. ncbi request reprint Pd-catalyzed carbonylative lactamization: a novel synthetic approach to FR900482
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Org Lett 6:1745-8. 2004
    ..reaction--see text]..
  101. ncbi request reprint On the diastereoselectivity of ru-catalyzed [5 + 2] cycloadditions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 5:4149-51. 2003
    ..reaction: see text]. Ru-catalyzed cycloisomerization of cyclopropylenynes proceeds with good to high diastereoselectivities to form hexahydroazulenes...

Research Grants1

  1. Synthesis of Macrolides, Steroids, Cyclopentanoids, etc.
    BARRY TROST; Fiscal Year: 2009
    ..These new synthetic methods apply to many structural types beyond those illustrated and constitutes a significant to gain access to complex molecular targets more easily. ..