G E Keck

Summary

Affiliation: University of Utah
Country: USA

Publications

  1. ncbi request reprint Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for beta-keto ester dianions
    G E Keck
    Department of Chemistry, University of Utah, Salt Lake City 84112 0850, USA
    Org Lett 1:289-91. 1999
  2. pmc Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 10:4783-6. 2008
  3. pmc Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 8:3667-70. 2006
  4. pmc Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah, 84112, USA
    J Org Chem 73:9675-91. 2008
  5. pmc Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 7:2153-6. 2005
  6. pmc The bryostatin 1 A-ring acetate is not the critical determinant for antagonism of phorbol ester-induced biological responses
    Gary E Keck
    University of Utah, Department of Chemistry, Salt Lake City, Utah 84112, USA
    Org Lett 11:2277-80. 2009
  7. pmc Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
    J Org Chem 70:2543-50. 2005
  8. pmc Intramolecular Baylis-Hillman and morita reactions using unsaturated thiol ester substrates containing enolizable aldehydes
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112 0850, USA
    Org Lett 4:3687-90. 2002
  9. pmc Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City 84112 0850, USA
    Org Lett 4:3131-4. 2002
  10. pmc Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
    Org Lett 4:1189-92. 2002

Collaborators

Detail Information

Publications21

  1. ncbi request reprint Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for beta-keto ester dianions
    G E Keck
    Department of Chemistry, University of Utah, Salt Lake City 84112 0850, USA
    Org Lett 1:289-91. 1999
    ..The products are convertible to beta-keto esters by oxidative cleavage of the olefin. These reactions thus provide a useful catalytic enantioselective method for chain extension with introduction of a versatile four-carbon unit...
  2. pmc Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 10:4783-6. 2008
    ..This overall approach was successfully employed in the preparation of a functionalized aza-spirocycle...
  3. pmc Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 8:3667-70. 2006
    ..The key features of the approach include the convergent fragment assembly with a highly stereoselective construction of the C7-C8 bond indicated above...
  4. pmc Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah, 84112, USA
    J Org Chem 73:9675-91. 2008
    ..Other key reactions in the synthesis include a stereoselective SmI(2) reduction of a beta-hydroxy ketone and a critical opening of a valerolactone with aniline which required extensive investigation...
  5. pmc Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 7:2153-6. 2005
    ..The key features of the route include BITIP-catalyzed asymmetric allylation reactions and Mukaiyama aldol reactions, a chelation-controlled allylation, pyran annulation reactions, and macrolactonization...
  6. pmc The bryostatin 1 A-ring acetate is not the critical determinant for antagonism of phorbol ester-induced biological responses
    Gary E Keck
    University of Utah, Department of Chemistry, Salt Lake City, Utah 84112, USA
    Org Lett 11:2277-80. 2009
    ..Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1...
  7. pmc Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
    J Org Chem 70:2543-50. 2005
    ....
  8. pmc Intramolecular Baylis-Hillman and morita reactions using unsaturated thiol ester substrates containing enolizable aldehydes
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112 0850, USA
    Org Lett 4:3687-90. 2002
    ..These can be used successfully for the preparation of both cyclopentenols and cyclohexenols, but the results are very sensitive to substrate and precise reaction conditions...
  9. pmc Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City 84112 0850, USA
    Org Lett 4:3131-4. 2002
    ..Either the syn or anti 1,3-amino alcohols can be obtained as the major product due to a divergence in selectivity with different N-protecting groups...
  10. pmc Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans
    Gary E Keck
    Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
    Org Lett 4:1189-92. 2002
    ....
  11. ncbi request reprint Total synthesis of the immunosupressant (-)-pironetin (PA48153C)
    G E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 3:707-10. 2001
    ....
  12. ncbi request reprint The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups
    G E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 2:2307-9. 2000
    ..Experiments with deuterated methanol show that the stereoselectivity arises from protonation of a samarium carbanion intermediate...
  13. ncbi request reprint A versatile preparation of alpha,beta-unsaturated lactones from homoallylic alcohols
    G E Keck
    Department of Chemistry, University of Utah, Salt Lake City 84112 0850, USA
    Org Lett 1:411-3. 1999
    ..The observations are consistent with a pathway involving an initial aldol condensation with subsequent acyl migration, lactonization, and beta-elimination and not an enolate equilibration-aldol mechanism...
  14. pmc Convergent assembly of highly potent analogues of bryostatin 1 via pyran annulation: bryostatin look-alikes that mimic phorbol ester function
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112, USA
    J Am Chem Soc 130:6660-1. 2008
    ..This tricyclic intermediate was elaborated to bryostatin analogues which displayed nanomolar to subnanomolar affinity for PKC, but displayed properties indistinguishable from a phorbol ester in a proliferation/attachment assay...
  15. pmc A catalytic asymmetric vinylogous Mukaiyama aldol reaction
    Lars V Heumann
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 9:4275-8. 2007
    ..A vinylogous Mukaiyama aldol reaction, conducted using 10 mol % of a BITIP catalyst and B(OMe)3 as an additive, effects an enantioselective four-carbon chain extension to give versatile E-alpha,beta-unsaturated thiol esters...
  16. pmc Total synthesis of bryostatin 1
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, Room 2020, Salt Lake City, Utah 84112, United States
    J Am Chem Soc 133:744-7. 2011
    ..Further elaborations of the resulting very highly functionalized intermediate include macrolactonization and selective cleavage of just one of five ester linkages present...
  17. pmc Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112 0850, USA
    Org Lett 7:2149-52. 2005
    ..The key features of this route include a BITIP-catalyzed asymmetric allylation reaction, chelation-controlled allylations, a hydroformylation reaction, and a pyran annulation reaction...
  18. pmc A new construction of 2-alkoxypyrans by an acylation-reductive cyclization sequence
    Lars V Heumann
    Department of Chemistry, University of Utah, Salt Lake City, UT 84112 0850, USA
    Org Lett 9:1951-4. 2007
    ..In this approach, two fragments are joined by esterification, and a subsequent intramolecular reductive cyclization affords the 2-hydroxypyran...
  19. pmc Total synthesis of (+)-dactylolide
    Carina C Sanchez
    Department of Chemistry, University of Utah, Salt Lake City, 84112 0850, USA
    Org Lett 7:3053-6. 2005
    ..The key features of this route include a catalytic asymmetric allylation, a diastereoselective pyran annulation, and a Horner-Wadsworth-Emmons macrocyclization...
  20. pmc Substitution on the A-ring confers to bryopyran analogues the unique biological activity characteristic of bryostatins and distinct from that of the phorbol esters
    Gary E Keck
    Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112, USA
    Org Lett 11:593-6. 2009
    ..Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA...
  21. pmc A new method for the synthesis of H(4)-BINOL
    Lars V Heumann
    Department of Chemistry, University of Utah, Salt Lake City, UT 84112 0850, USA
    J Org Chem 73:4725-7. 2008
    ..The key step is the net partial hydrogenation of (R)-BINOL made possible by prior bis-etherification of the parent BINOL...