BARRY TROST

Summary

Affiliation: Stanford University
Country: USA

Publications

  1. ncbi request reprint Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:2846-7. 2005
  2. pmc Cyclic 1,2-diketones as core building blocks: a strategy for the total synthesis of (-)-terpestacin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 16:6265-77. 2010
  3. pmc Access to a welwitindolinone core using sequential cycloadditions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 11:3782-5. 2009
  4. doi request reprint Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates
    Barry M Trost
    Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305 5080, USA
    J Org Chem 74:5115-7. 2009
  5. pmc Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 11:2539-42. 2009
  6. doi request reprint Regio- and enantioselective synthesis of pyrrolidines bearing a quaternary center by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethanes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 135:2459-61. 2013
  7. doi request reprint Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 52:1523-6. 2013
  8. pmc Total synthesis of aeruginosin 98B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:18944-7. 2012
  9. pmc Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:5632-5. 2012
  10. pmc Asymmetric catalytic synthesis of the proposed structure of trocheliophorolide B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:4698-700. 2012

Detail Information

Publications103 found, 100 shown here

  1. ncbi request reprint Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:2846-7. 2005
    ..For the first time, asymmetric creation of tertiary centers occurs with high ee (78-99%). The different results between this reaction and the use of lithium or tin enolates suggest different mechanisms may be involved...
  2. pmc Cyclic 1,2-diketones as core building blocks: a strategy for the total synthesis of (-)-terpestacin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 16:6265-77. 2010
    ..During our exploration many interesting chemoselectivity issues have been addressed, such as a highly selective ring-closing metathesis and a challenging oxidation of a disubstituted olefin in the presence of three trisubstituted ones...
  3. pmc Access to a welwitindolinone core using sequential cycloadditions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 11:3782-5. 2009
    ..3.1]decadiene. Subsequent modifications to the cycloadduct allowed for an intramolecular [4 + 2] cycloaddition to generate the oxindole and complete the core of the natural product family...
  4. doi request reprint Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates
    Barry M Trost
    Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305 5080, USA
    J Org Chem 74:5115-7. 2009
    ..Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carboxylate reagents. This reaction provides ready access to N-carbamoyl-3-monosubstituted oxindoles...
  5. pmc Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 11:2539-42. 2009
    ..Enones and enals derived from the [IndRu(PPh(3))(2)Cl]-catalyzed redox isomerization of primary and secondary propargyl alcohols undergo a subsequent intramolecular conjugate addition to provide cyclic ethers in excellent yields...
  6. doi request reprint Regio- and enantioselective synthesis of pyrrolidines bearing a quaternary center by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethanes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 135:2459-61. 2013
    ....
  7. doi request reprint Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford CA 94305 5080 USA http www stanford edu group bmtrost
    Angew Chem Int Ed Engl 52:1523-6. 2013
    ..This is a conceptually and mechanistically distinct strategy from traditional methods for the synthesis of enantioenriched allylic substitution products. 2,6-DMBQ=2,6-dimethylbenzoquinone...
  8. pmc Total synthesis of aeruginosin 98B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 134:18944-7. 2012
    ..The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1...
  9. pmc Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:5632-5. 2012
    ..The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer...
  10. pmc Asymmetric catalytic synthesis of the proposed structure of trocheliophorolide B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:4698-700. 2012
    ..Comparison with the reported data suggests a misassignment of the natural product structure...
  11. doi request reprint Synthesis of α-allylated α,β-unsaturated carbonyl compounds using vanadium/palladium contemporaneous dual catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California, USA
    Nat Protoc 7:1497-501. 2012
    ..0 h for isolation and purification. This chemistry has been applied to obtain a wide range of α-allylated α,β-unsaturated ketones, esters and amides, which are highly valuable building blocks in organic synthesis...
  12. pmc Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, United States
    Org Lett 14:2254-7. 2012
    ..A nitropyrrole-containing nucleoside analogue was synthesized in seven steps to demonstrate the synthetic utility of this transformation...
  13. pmc Total synthesis of laulimalide: synthesis of the northern and southern fragments
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Chemistry 18:2948-60. 2012
    ..This reaction proved to be selective for the formation of a six-membered ring, over a seven. The use of an electron-deficient bidentate phosphine allowed for the reaction to proceed with a reduced catalyst loading...
  14. pmc Enantioselective palladium-catalyzed [3 + 2] cycloadditions of trimethylenemethane with nitroalkenes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 14:234-7. 2012
    ..Furthermore, the products thus formed are highly versatile synthetic intermediates and provide convenient access to both cyclopentylamines and cyclopentenones...
  15. ncbi request reprint A convergent Pd-catalyzed asymmetric allylic alkylation of dl- and meso-divinylethylene carbonate: enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 13:9547-60. 2007
    ..A mechanism for this intriguing transformation is proposed and a concise enantioselective total synthesis of (+)-australine hydrochloride is reported as well as a formal synthesis of isoaltholactone...
  16. ncbi request reprint Total synthesis of spirotryprostatin B via diastereoselective prenylation
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 0508, USA
    Org Lett 9:2763-6. 2007
    ..The decarboxylation-alkylation of a series of substituted beta-keto esters is described, demonstrating the broad scope of this class of pronucleophiles and allylating agents...
  17. pmc Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:12398-9. 2007
  18. ncbi request reprint Rhodium-catalyzed cycloisomerization: formation of indoles, benzofurans, and enol lactones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 46:2074-7. 2007
  19. pmc Enantioselective synthesis of alpha-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:282-3. 2007
  20. ncbi request reprint Asymmetric synthesis of alpha-substituted aldehydes by Pd-catalyzed asymmetric allylic alkylation-alkene isomerization-Claisen rearrangement
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 8:6007-10. 2006
    ..Remarkable chemoselectivity in the olefin isomerization step was observed. An asymmetric synthesis of communiol A was accomplished applying this methodology...
  21. pmc Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 9:1473-6. 2007
    ....
  22. pmc Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 128:13328-9. 2006
    ..Yields of exo-methylenecyclopentane products range from 59 to 99%, and enantiomeric excesses range from 58 to 92% ee...
  23. pmc Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: an asymmetric Wagner-Meerwein shift
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 128:6044-5. 2006
    ..In addition, we obtained excellent diastereoselectivity and enantioselectivity at the same time by using 3-monosubstituted allenylcyclobutanol...
  24. pmc A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst: synthesis of either anti- or syn-alpha-hydroxy-beta-amino ketones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 128:2778-9. 2006
    ..The dependence of the diastereoselectivity on the nature of the N-substituent presumably arises from the steric demands of the diphenylphosphinoyl group...
  25. ncbi request reprint S,O-acetals as novel "chiral aldehyde" equivalents
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 12:2171-87. 2006
    ..The synthetic value of this process was exemplified by subsequent transformations of the diols including the development of a one-pot dihydroxylation-deprotective acyl migration protocol to give differentially protected 1,2-diols...
  26. pmc Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:17921-37. 2005
    ..This work was also an opportunity to further probe the scope of the ruthenium-catalyzed alkene-alkyne coupling, in particular using enynes, and studies using various functionalized substrates are described...
  27. ncbi request reprint Dynamic kinetic asymmetric allylic alkylations of allenes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 127:14186-7. 2005
    ....
  28. ncbi request reprint A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 7:4761-4. 2005
    ..Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran...
  29. ncbi request reprint Enantioselective palladium-catalyzed addition of 1,3-dicarbonyl compounds to an allene derivative
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 11:7075-82. 2005
    ..Thus, a mixture of triethylamine and benzoic acid proved optimal (ee's 93-99). Employment of the (R,R)-phenyl Trost ligand gave a product with S configuration. A model to rationalize the results has been developed...
  30. ncbi request reprint Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:13598-610. 2005
    ..The spectroscopic data for the synthetic and natural material are in excellent agreement...
  31. doi request reprint Asymmetric Friedel-Crafts alkylation of pyrroles with nitroalkenes using a dinuclear zinc catalyst
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:2438-9. 2008
  32. doi request reprint Coupling of alkenes and alkynes: synthesis of the C1-C11 And C18-C28 fragments of miyakolide
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 10:1893-6. 2008
    ..The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry...
  33. pmc Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 14:7648-57. 2008
    ..The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities...
  34. pmc The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 133:20611-22. 2011
    ....
  35. pmc Acetoxy Meldrum's acid: a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 13:3222-5. 2011
    ..These scaffolds were used to complete formal syntheses of the anti-HIV drugs carbovir, abacavir, and the antibiotic aristeromycin...
  36. pmc A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 133:8502-5. 2011
    ..Importantly, the method tolerates a wide range of functionality, including allylic carbonates and carbamates, and thus allows for rapid elaboration of the β-alkynyl esters into a variety of chiral, substituted heterocycles...
  37. doi request reprint Propargyl alcohols as β-oxocarbenoid precursors for the ruthenium-catalyzed cyclopropanation of unactivated olefins by redox isomerization
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 133:4766-9. 2011
    ..Furthermore, a rare case of a formal vinylic C-H insertion reaction is described...
  38. pmc Development of a concise synthesis of (-)-oseltamivir (Tamiflu)
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 17:3630-43. 2011
    ..Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA) as well as a rhodium-catalyzed chemo-, regio-, and stereoselective aziridination reaction...
  39. doi request reprint An atom-economical access to β-heteroarylated ketones from propargylic alcohols via tandem ruthenium/indium catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    Org Lett 13:398-401. 2011
    ..Both electron-rich and neutral heteroarenes, such as furans and indoles, efficiently undergo the redox isomerization/conjugate addition (RICA) sequence to provide the corresponding adducts in yields of up to 97%...
  40. pmc An atom-economic synthesis of nitrogen heterocycles from alkynes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, United States
    J Am Chem Soc 133:740-3. 2011
    ..Control over the reaction conditions provides ready access to isopyrroles, 2,3,4-trisubstituted pyrroles, and 3-substituted pyrollidin-2-ones...
  41. pmc Total synthesis of bryostatin 16 using a Pd-catalyzed diyne coupling as macrocyclization method and synthesis of C20-epi-bryostatin 7 as a potent anticancer agent
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, United States
    J Am Chem Soc 132:16403-16. 2010
    ..Preliminary biological studies indicated that this new analogue exhibits nanomolar anti-cancer activity against several cancer cell lines...
  42. pmc The direct catalytic asymmetric aldol reaction
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chem Soc Rev 39:1600-32. 2010
    ..New methods have improved the reactivity, selectivity and substrate scope of the direct aldol reaction and enabled the synthesis of complex molecular targets (357 references)...
  43. ncbi request reprint Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 132:15534-6. 2010
    ..This methodology represents a novel asymmetric carbon-carbon bond formation between a benzyl group and a prochiral nucleophile to generate a quaternary center...
  44. pmc Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6 + 3] trimethylenemethane cycloaddition with tropones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:14960-1. 2008
    ..3.1]decadienes in excellent regio-, diastereo-, and enantioselectivity. Products of the Pd-TMM [6 + 3] cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to yield bicyclo[3.3.2]decadienes in good yield...
  45. pmc An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:11970-8. 2008
    ..Application of this method to the synthesis of leukotriene B4 demonstrates its utility and extraordinary selectivity...
  46. pmc An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 127:10028-38. 2005
    ..The sequences constitute the equivalent of stereoselective aldol, homo-aldol, and bishomo-aldol type processes. The method is applied to a short synthesis of the piperidine alkaloid, spectaline...
  47. ncbi request reprint Regioselectivity control in a ruthenium-catalyzed cycloisomerization of diyne-ols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 6:4235-8. 2004
    ..This regioselectivity of the cyclization can be controlled by the choice of solvent system. DFT calculations confirm the expected greater stability of the silyl-pyrans relative to the acylsilanes...
  48. ncbi request reprint 5H-oxazol-4-ones as building blocks for asymmetric synthesis of alpha-hydroxycarboxylic acid derivatives
    Barry M Trost
    Department of Chemistry, Stanford Univeristy, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:1944-5. 2004
    ..The presence of a double bond in the product allows them to be further modified via the chemistry of the double-bond, including metathesis. The products are hydrolyzed under basic conditions to provide alpha-hydroxyamides...
  49. ncbi request reprint An efficient enantioselective synthesis of (-)-galanthamine
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:2795-7. 2002
  50. ncbi request reprint Chemoselectivity of the ruthenium-catalyzed hydrative diyne cyclization: total synthesis of (+)-cylindricine C, D, and E
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 5:4599-602. 2003
    ..reaction: see text] The chemoselectivity of the ruthenium-catalyzed hydrative diyne cylization is explored in an expeditious synthesis of the tricyclic alkaloids cylindricine C, D, and E...
  51. ncbi request reprint Dynamic kinetic asymmetric cycloadditions of isocyanates to vinylaziridines
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 125:11836-7. 2003
    ..The reactivity pattern is consistent with a Curtin-Hammett situation wherein the enantiodiscriminating event is the cyclization of a rapidly equilibrating dynamic pi-allyl palladium intermediate...
  52. ncbi request reprint Palladium-catalyzed asymmetric allylic alkylation of alpha-aryl ketones
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:3492-5. 2002
  53. ncbi request reprint Asymmetric synthesis of oxygen heterocycles via Pd-catalyzed dynamic kinetic asymmetric transformations: application to nucleosides
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 9:4442-51. 2003
    ..One advantage of this strategy is the easy access to either enantiomeric series, both of which have important biological applications...
  54. ncbi request reprint Regioselective hydrosilylation of propargylic alcohols: an aldol surrogate
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 42:3415-8. 2003
  55. ncbi request reprint Intramolecular palladium-catalyzed allylic alkylation: enantio- and diastereoselective synthesis of [2.2.2] bicycles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Org Lett 4:3427-30. 2002
    ..Pd-catalyzed asymmetric allylic alkylation provides both enantio- and diastereoselectivity in formation of bicyclo [2.2.2] octan-2,3-diones and quinuclidin-2-ones, the latter potential precursors to quinine alkaloids. [reaction: see text]..
  56. ncbi request reprint Stereocontrolled synthesis of (+)-boronolide
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Org Lett 4:3513-6. 2002
    ..Ring closing metathesis provides the lactone ring. The synthesis requires 12 steps and proceeds in 26% overall yield. [reaction: see text]..
  57. ncbi request reprint Ruthenium-catalyzed alkene-alkyne coupling: synthesis of the proposed structure of amphidinolide A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 124:12420-1. 2002
    ..Notably, the Ru-catalyzed macrocyclization to this macrolide proceeded in better yields than either a Pd-catalyzed cross-coupling or a Ru-catalyzed metathesis, macrocylization methods for the other two total synthesis...
  58. ncbi request reprint An efficient one-pot enantio- and diastereoselective synthesis of heterocycles
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:4693-7. 2002
  59. ncbi request reprint Callipeltoside A: assignment of absolute and relative configuration by total synthesis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:841-3. 2002
  60. ncbi request reprint Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Org Lett 5:1563-5. 2003
    ..reaction: see text]..
  61. ncbi request reprint Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:2660-1. 2004
    ..It could be shown that this reversal in enantioselectivity is due to formation of a new catalytic species which incorporates the aldol product...
  62. ncbi request reprint AAA in KAT/DYKAT processes: first- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol
    B M Trost
    Department of Chemistry, Stanford University, CA 94305 5080, USA
    Chemistry 7:3768-75. 2001
    ..The utility of effecting KAT/DYKAT processes through the Pd-catalyzed AAA reaction is demonstrated by efficient syntheses of both enantiomers of the potent glycosidase inhibitor cyclophellitol...
  63. ncbi request reprint Ruthenium-catalyzed enyne cycloisomerizations. Effect of allylic silyl ether on regioselectivity
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 126:15592-602. 2004
    ..Furthermore, examples of stereoinduction are shown and lead to highly substituted carbo- and heterocycles with excellent diastereocontrol...
  64. pmc Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 129:12396-7. 2007
  65. ncbi request reprint Palladium-catalyzed asymmetric allylic alkylation of ketone enolates
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Chemistry 11:174-84. 2004
    ..The quaternary substituted products available by this method are versatile substrates for further elaboration...
  66. ncbi request reprint Synthetic stitching with silicon: geminal alkylation-hydroxylation of alkynyl carbonyl compounds
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:13942-4. 2004
    ..Good diastereoselection (>10:1) is observed for substrates bearing gamma-alkoxy stereocenters...
  67. ncbi request reprint A three-component coupling approach to cyclopentanoids
    B M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Org Chem 66:7714-22. 2001
    ..Further applicability of this strategy is shown in the total syntheses of tetrahydrodicranenone B, rosaprostol, and a selective COX-2 inhibitor...
  68. ncbi request reprint Alkene-alkyne coupling as a linchpin: an efficient and convergent synthesis of amphidinolide P
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:13618-9. 2004
    ..The target structure was prepared in 15 steps for the longest linear sequence and 10% overall yield, 24 steps total...
  69. ncbi request reprint Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 7:2097-9. 2005
    ..The utility of this method has been demonstrated by SO2 extrusion of 3-sulfolenes to afford 1,3-dienes and the subsequent inter- and intramolecular Diels-Alder reaction...
  70. ncbi request reprint Structure elucidation of (+)-amphidinolide a by total synthesis and NMR chemical shift analysis
    Barry M Trost
    Department of Chemistry, Stanford University, California 93405 5080, USA
    J Am Chem Soc 126:5028-9. 2004
    ..The key step, a [Cp*Ru(MeCN)3]PF6-catalyzed alkene-alkyne coupling, was used to form the 20-membered ring in the final step of the synthesis...
  71. ncbi request reprint Synthesis of allenamides by copper-catalyzed coupling of allenyl halides with amides, carbamates, and ureas
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 7:2117-20. 2005
    ..The reactions proceed in good to excellent yield using 7 mol % copper thiophenecarboxylate and 15 mol % of a diamine catalyst...
  72. ncbi request reprint Application of the AAA reaction to the synthesis of the furanoside of C-2-epi-hygromycin A: a total synthesis of C-2-epi-hygromycin A
    Barry M Trost
    Department of Chemistry, Stanford University, CA 94305 5080, USA
    Chemistry 8:259-68. 2002
    ..The utility of a phenol as a nucleophile in the Pd catalyzed glycosylation is demonstrated. From this strategy emerged a short, practical synthesis of C-2-epi-hygromycin A...
  73. ncbi request reprint Polymer-supported C2-symmetric ligands for palladium-catalyzed asymmetric allylic alkylation reactions
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    Angew Chem Int Ed Engl 41:4691-3. 2002
  74. ncbi request reprint A Rh(I)-catalyzed cycloisomerization of homo- and bis-homopropargylic alcohols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 125:7482-3. 2003
    ..The method provides access to useful aminosugars. A mechanism to account for the different selectivity of this catalyst as compared to others is proposed...
  75. pmc Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 132:5186-92. 2010
    ..Additionally, the development of this method allowed for the rapid total syntheses of several biologically important diynol-containing natural products...
  76. ncbi request reprint A Ru catalyzed divergence: oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, CA 94305 5080, USA
    J Am Chem Soc 124:2528-33. 2002
    ..The utility of the cycloisomerization to dihydropyrans is demonstrated by an iterative process leading to the antiviral agent narbosine B. A rationale for this dramatic switch by simple ligand modification is proposed...
  77. ncbi request reprint An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 124:4178-9. 2002
    ..Furthermore, 3-hydroxy-1,6-diynes also can be cyclized to form cross-conjugated aldehydes...
  78. ncbi request reprint On inventing reactions for atom economy
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Acc Chem Res 35:695-705. 2002
    ..Using mechanistic reasoning, over 20 new processes of varying complexity have been designed and implemented. While some involved oxidation-reduction processes, most involved C-C bond-forming reactions...
  79. ncbi request reprint Mechanistic dichotomy in CpRu(CH(3)CN)(3)PF(6) catalyzed enyne cycloisomerizations
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California, 94305, USA
    J Am Chem Soc 124:5025-36. 2002
    ..In the latter case, a C-H insertion to form a pi-allylruthenium intermediate is proposed and supported by deuterium-labeling studies. A rationale is presented for the structural dependence of the mechanism...
  80. ncbi request reprint An asymmetric synthesis of hamigeran B via a Pd asymmetric allylic alkylation for enantiodiscrimination
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 126:4480-1. 2004
    ..Such unusual behavior speaks to the unusual chemical properties associated with hamigeran B which may be relevant to its biological activity...
  81. pmc Total synthesis of (-)-pseudolaric acid B
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 130:16424-34. 2008
    ..The easy formation of an oxo-bridged derivative was the major hurdle to the completion of the synthesis and showcased the intriguing reactivity of the complex core of the pseudolaric acids...
  82. pmc Ruthenium- and palladium-catalyzed enyne cycloisomerizations: differentially stereoselective syntheses of bicyclic structures
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Am Chem Soc 130:16176-7. 2008
    ..A number of substrates are investigated, and the outcomes ultimately offer a clear mechanistic rationale for these observations...
  83. pmc Total synthesis and stereochemical assignment of (-)-ushikulide A
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California, 94305 5080, USA
    J Am Chem Soc 131:15061-74. 2009
    ..These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies...
  84. pmc Si-based benzylic 1,4-rearrangement/cyclization reaction
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    Org Lett 11:511-3. 2009
    ..The trans-selective hydrosilylation of ynones (1) yields beta-silylated enones (2) that undergo a benzylic 1,4-rearrangement/cyclization reaction in the presence of base, yielding 2,5-dihydro-1,2-oxasiloles (3)...
  85. pmc Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 131:4572-3. 2009
    ..The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity...
  86. 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...
  87. 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...
  88. 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]..
  89. 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...
  90. 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
    ....
  91. 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...
  92. ncbi request reprint Formation of vinyl halides via a ruthenium-catalyzed three-component coupling
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305, USA
    J Am Chem Soc 124:7376-89. 2002
    ..The vinyl halides have been shown to be precursors to alpha-hydroxy ketones and cyclopentenones, and as coupling partners in Suzuki-type reactions...
  93. ncbi request reprint A chemoselective reduction of alkynes to (E)-alkenes
    Barry M Trost
    Department of Chemistry, Stanford University, Stanford, California 94305 5080, USA
    J Am Chem Soc 124:7922-3. 2002
    ..The reaction is compatible with many sensitive functional groups and provides a general trans-alkyne reduction not possible by other means...
  94. 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...
  95. 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
  96. 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...
  97. 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...
  98. 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...
  99. 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...
  100. 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...
  101. 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...

Research Grants37

  1. NOVEL APPROACHES TO ANTITUMOR AND ANTIVIRAL AGENTS
    BARRY TROST; Fiscal Year: 2004
    ..By accessing a very diverse range of structural types, the best opportunities to discover new therapeutic agents arise. ..
  2. SYNTHESIS OF MACROCYCLES STEROIDS CYCLOPENTANOIDS ETC
    BARRY TROST; Fiscal Year: 2001
    ..Ring expansion methods may convert these cores into the taxoid skeleton with appropriate functionality at key points for analog development. ..
  3. Synthesis of Macrolides. Steroids, Cyclopentanoids, etc
    BARRY TROST; Fiscal Year: 2005
    ..This new concept sets the stage for solutions to a long standing problem, the ion channel blockers, the grayanotoxins. as well as the more recently discovered rameswaralide, a potent antiinflamatory. ..
  4. Synthesis of Macrolides, Steroids, Cyclopentanoids, etc.
    BARRY TROST; Fiscal Year: 2006
    ..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. ..
  5. NOVEL SYNTHETIC APPROACHES TO ANTITUMOR COMPOUNDS
    BARRY TROST; Fiscal Year: 1992
    ..A strategy to one family of tumor promoters represented by teleocidin explores the concept of chemical chameleons. In most cases, the strategy also considers the problem of absolute stereochemistry...
  6. NOVEL APPROACHES TO ANTITUMOR AND ANTIVIRAL AGENTS
    BARRY TROST; Fiscal Year: 1993
    ..The diversity of the challenges posed by antiviral and antitumor agents represent highly meaningful tests of their use...
  7. Synthesis of Macrolides, Steroids, Cyclopentanoids, etc.
    BARRY TROST; Fiscal Year: 2007
    ..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. ..
  8. Synthesis of Macrolides, Steroids, Cyclopentanoids, etc.
    BARRY TROST; Fiscal Year: 2007
    ..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. ..
  9. Novel Approaches for Antitumor and Antiviral Agents
    Barry M Trost; Fiscal Year: 2010
    ..This proposal helps to address this key challenge by developing the underlying initial technology within classes of compounds having demonstrably antitumor or antiviral activities. ..
  10. NOVEL APPROACHES TO ANTITUMOR AND ANTIVIRAL AGENTS
    BARRY TROST; Fiscal Year: 2007
    ..By expediting access to very diverse arrays of structural types, the best opportunities to discover new therapeutic agents arise. ..
  11. 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. ..
  12. NOVEL APPROACHES TO ANTITUMOR AND ANTIVIRAL AGENTS
    BARRY TROST; Fiscal Year: 2000
    ..Equally important, new avenues to vary structure around these cores in order to establish structure-activity relationships with the aim to create better therapeutic agents become available. ..