James A Marshall

Summary

Affiliation: University of Virginia
Country: USA

Publications

  1. ncbi request reprint Total synthesis of bafilomycin V(1): a methanolysis product of the macrolide bafilomycin C(2)
    James A Marshall
    Department of Chemistry, University of Virginia, McCormick Road, P O Box 400319, Charlottesville, Virginia 22904, USA
    J Org Chem 67:733-40. 2002
  2. ncbi request reprint Chiral allylic and allenic metal reagents for organic synthesis
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 72:8153-66. 2007
  3. ncbi request reprint Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 8:5505-8. 2006
  4. ncbi request reprint Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: unambiguous confirmation of absolute stereochemistry
    J A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, USA
    J Nat Prod 62:1123-7. 1999
  5. ncbi request reprint Diastereoselective additions of chiral vinylzinc reagents to alpha-chiral aldehydes
    James A Marshall
    Department of Chemistry, University of Virginia, PO Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 6:445-8. 2004
  6. ncbi request reprint Synthesis of a C20-C26 segment of superstolide A by addition of a chiral allenylzinc reagent to (R)-N-boc alaninal
    James A Marshall
    Department of Chemistry, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 7:1593-6. 2005
  7. ncbi request reprint Synthesis of cis- and trans-2,5-disubstituted tetrahydrofurans by a tandem dihydroxylation-SN2 cyclization sequence
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, 22904, USA
    Org Lett 7:4819-22. 2005
  8. ncbi request reprint Synthesis of the C6-C21 segment of amphidinolide E
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 7:5331-3. 2005
  9. ncbi request reprint Leptostatin: a synthetic hybrid of the cytotoxic polyketides callystatin A and leptomycin B
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, VA 22904, USA
    Bioorg Med Chem Lett 16:320-3. 2006
  10. ncbi request reprint (R)- and (S)-4-TIPS-3-butyn-2-ol. Useful precursors of chiral allenylzinc and indium reagents
    James A Marshall
    Department of Chemistry, University of Virginia, McCormick Road, P O Box 400319, Charlottesville, Virginia 22904 4319, USA
    J Org Chem 71:4840-4. 2006

Research Grants

Collaborators

Detail Information

Publications30

  1. ncbi request reprint Total synthesis of bafilomycin V(1): a methanolysis product of the macrolide bafilomycin C(2)
    James A Marshall
    Department of Chemistry, University of Virginia, McCormick Road, P O Box 400319, Charlottesville, Virginia 22904, USA
    J Org Chem 67:733-40. 2002
    ..Attempted cyclization of several C15 hydroxy acid derivatives to the 16-membered lactone bafilomycin A(1), a potent inhibitor of vacuolar ATPases, could not be achieved...
  2. ncbi request reprint Chiral allylic and allenic metal reagents for organic synthesis
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 72:8153-66. 2007
    ..This account traces the evolution of our work on the synthesis of chiral allylic and allenic organometal compounds of tin, silicon, zinc, and indium and their application to natural product synthesis over the past quarter century...
  3. ncbi request reprint Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 8:5505-8. 2006
    ..Conjugated aldehydes undergo smooth Pd(OAc)2.PPh3- or Me2CuCNLi2-catalyzed 1,4-addition of dialkylzinc reagents. [reaction: see text]...
  4. ncbi request reprint Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: unambiguous confirmation of absolute stereochemistry
    J A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, USA
    J Nat Prod 62:1123-7. 1999
    ..Removal of the three MOM protecting groups was achieved with aqueous HCl in THF. The 10(R) diastereomer was found to correspond to natural asimin...
  5. ncbi request reprint Diastereoselective additions of chiral vinylzinc reagents to alpha-chiral aldehydes
    James A Marshall
    Department of Chemistry, University of Virginia, PO Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 6:445-8. 2004
    ....
  6. ncbi request reprint Synthesis of a C20-C26 segment of superstolide A by addition of a chiral allenylzinc reagent to (R)-N-boc alaninal
    James A Marshall
    Department of Chemistry, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 7:1593-6. 2005
    ..Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts...
  7. ncbi request reprint Synthesis of cis- and trans-2,5-disubstituted tetrahydrofurans by a tandem dihydroxylation-SN2 cyclization sequence
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, 22904, USA
    Org Lett 7:4819-22. 2005
    ..reaction: see text] Dihydroxylation of delta- and epsilon-mesyloxy alpha,beta-unsaturated esters proceeds with in situ cyclization to afford 2,5-disubstituted and 2,3,5-trisubstituted tetrahydrofurans...
  8. ncbi request reprint Synthesis of the C6-C21 segment of amphidinolide E
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 7:5331-3. 2005
    ..reaction: see text] A convergent approach to a C6-C21 segment of the polyketide amphidinolide E has been developed through combination of three subunits by allenylindium bromide-aldehyde addition and Suzuki sp2-sp3 coupling...
  9. ncbi request reprint Leptostatin: a synthetic hybrid of the cytotoxic polyketides callystatin A and leptomycin B
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, VA 22904, USA
    Bioorg Med Chem Lett 16:320-3. 2006
    ..Like their natural counterparts, these hybrids exhibit nanomolar levels of cytotoxicity toward HCT-116 human colon cancer cells...
  10. ncbi request reprint (R)- and (S)-4-TIPS-3-butyn-2-ol. Useful precursors of chiral allenylzinc and indium reagents
    James A Marshall
    Department of Chemistry, University of Virginia, McCormick Road, P O Box 400319, Charlottesville, Virginia 22904 4319, USA
    J Org Chem 71:4840-4. 2006
    ..Additions to alpha-substituted enals are highly diastereoselective, while beta,beta-disubstituted enals afford ca. 2:1 mixtures of anti and syn adducts...
  11. ncbi request reprint An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue
    James A Marshall
    Department of Chemistry, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 8:3557-60. 2006
    ..reaction: see text] A synthesis of the Annonaceous acetogenin asimicin and a side-chain analogue has been achieved by a highly convergent route in which Grubbs cross-metathesis plays a key role...
  12. ncbi request reprint Synthesis of a bistetrahydrofuran C17-C32 fragment of the polyether antibiotic ionomycin
    James A Marshall
    Department of Chemistry, University of Virginia, PO Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 8:4375-8. 2006
    ..A Zn-initiated triepoxide cascade cyclization reaction was employed for the synthesis of the bistetrahydrofuran core segment of the polyether ionophore antibiotic ionomycin...
  13. ncbi request reprint ABC synthesis and antitumor activity of a series of Annonaceous acetogenin analogs with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, VA 22904, USA
    Bioorg Med Chem Lett 17:2434-7. 2007
    ..Side-chain analogs of Annonaceous acetogenins with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit have been prepared and tested for cytotoxicity against HCT-116 human colon cancer cells...
  14. ncbi request reprint A formal synthesis of the callipeltoside aglycone
    James A Marshall
    Department of Chemistry, University of Virginia, PO Box 40019, Charlottesville, Virginia 22904, USA
    Org Lett 10:93-6. 2008
    ....
  15. doi request reprint A cascade cyclization route to adjacent bistetrahydrofurans from chiral triepoxyfarnesyl bromides
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, McCormick Road, Charlottesville, Virginia 22904, USA
    J Org Chem 73:6753-7. 2008
    ..A number of isomeric bistetrahydrofuran analogues were prepared from triepoxy farnesyl bromides by a zinc-initiated reduction-elimination and in situ Lewis acid-promoted cascade cyclization...
  16. ncbi request reprint Total synthesis and structure confirmation of leptofuranin D
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    J Org Chem 68:7428-32. 2003
    ..The synthesis was completed by oxidation of the unprotected alcohol of 42, followed by global desilylation and exposure of the resulting tetrol to MnO(2)...
  17. ncbi request reprint Synthesis of enantioenriched propargylic alcohols related to polyketide natural products. A comparison of methodologies
    James A Marshall
    Department of Chemistry, P O Box 400319 University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 5:3197-9. 2003
    ..Additions of TMS acetylene to alpha-chiral aldehydes, catalyzed by a Ti(O-i-Pr)(4)-BINOL complex, were diastereoselective but substrate dependent...
  18. ncbi request reprint Progress toward the total synthesis of bafilomycin A(1): stereoselective synthesis of the C15-C25 subunit by additions of nonracemic allenylzinc reagents to aldehydes
    J A Marshall
    Department of Chemistry, McCormick Road, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 2:2897-900. 2000
    ..reaction: see text] A highly stereoselective synthesis of the C15-C25 subunit (2) of bafilomycin A(1) (1) has been accomplished by a route utilizing additions of chiral nonracemic allenylzinc reagents to aldehydes...
  19. ncbi request reprint Synthesis of a C1-C21 subunit of the protein phosphatase inhibitor tautomycin: a formal total synthesis
    J A Marshall
    Department of Chemistry, McCormick Road, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 66:1373-9. 2001
    ..This ketone proved identical to an intermediate employed by Chamberlin in a prior total synthesis of tautomycin...
  20. ncbi request reprint Lipase-mediated resolution of 4-TMS-3-butyn-2-ol and use of the mesylate derivatives as a precursor to a highly stereoselective chiral allenylindium reagent
    J A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 3:3369-72. 2001
    ..The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts...
  21. ncbi request reprint Synthesis of stereopentad analogues of the C14-C22 segment of callystatin A through additions of chiral allenylzinc reagents to stereotriads
    J A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, VA 22904, USA
    J Org Chem 66:7825-31. 2001
    ..Significant mismatching was observed with the latter two aldehydes and the (M)-allenylzinc reagent. An evaluation of possible transition states is presented in consideration of steric and dipolar control elements...
  22. ncbi request reprint Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide
    J A Marshall
    Department of Chemistry, University of Virginia, PO Box 400319, Charlottesville, Virginia 22904, USA
    J Org Chem 66:8037-41. 2001
    ..The synthetic strategy was strongly directed by molecular mechanics calculations, which provided valuable insight into stereodefining steps including double bond stereochemistry and butenolide configuration...
  23. ncbi request reprint Coupling of alkynylTMS derivatives with vinylic iodides. An efficient route to 1,3-enynes and dienes
    J A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 3:4107-10. 2001
    ..Enynes prepared from homopropargylic alcohols undergo intramolecular hydrosilylation and subsequent silyl cleavage with TBAF to afford 1,3-dienes...
  24. ncbi request reprint Total synthesis of (-)-callystatin A
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 67:2751-4. 2002
    ..The route features chiral allenylmetal additions to construct the polypropionate C15-22 segment and an sp(2)-sp(3) Suzuki coupling to join the C1-C11 and C12-C22 subunits...
  25. ncbi request reprint Second-generation synthesis of the polypropionate subunit of callystatin A based on regioselective internal alkyne hydrostannation
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, McCormick Road, Charlottesville, Virginia 22904 4319, USA
    Org Lett 4:3931-4. 2002
    ..formula: see text] An improved route to the polypropionate segment of callystatin A is described in which the efficient directed hydrostannation of an internal alkyne and subsequent iodinolysis provides a key vinylic iodide intermediate...
  26. ncbi request reprint A modular synthesis of annonaceous acetogenins
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 68:1771-9. 2003
    ..The IC90 activities were ca. 10(-3) microM for asimicin and asimin but only 0.1-1 microM for bullanin and asiminocin...
  27. ncbi request reprint Total synthesis of (-)- and (+)-membrenone C
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 5:1729-32. 2003
    ....
  28. ncbi request reprint Synthesis of 2,5-disubstituted tetrahydrofurans by stereospecific elimination-cyclization of 1-iodomethyl-1,5-bis-epoxides
    James A Marshall
    Department of Chemistry, University of Virginia, P O Box 400319, Charlottesville, Virginia 22904, USA
    Org Lett 5:1931-3. 2003
    ..reaction: see text] Treatment of 1-iodomethyl-1,5-bis-epoxides with zinc in refluxing ethanol affords cis or trans 2-vinyl-5-(1-hydroxyethy)-substituted tetrahydrofurans stereospecifically in high yield...
  29. doi request reprint Synthesis of a lactone diastereomer of the cembranolide uprolide D
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    Org Lett 12:4328-31. 2010
    ..Unlike previous examples of allyl chromium additions, none of the Felkin-Anh derived adduct could be detected...
  30. ncbi request reprint Total synthesis and structure confirmation of the annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin a, and 5(R)-uvarigrandin a (narumicin I?)
    James A Marshall
    Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA
    J Org Chem 68:1780-5. 2003
    ..The synthetic 5(R)-uvarigrandin A is possibly identical to narumicin I, but subtle differences in the reported NMR spectra prevented an unambiguous assessment of this point...

Research Grants2

  1. SYNTHESIS OF ANNONACEOUS ACETOGENINS AND ANALOGUES
    James Marshall; Fiscal Year: 2001
    ..The synthetic approach will employ chiral allylic and allenic organometal reagents to introduce stereogenic centers with concurrent formation of carbon-carbon bonds. ..
  2. Synthesis of Tumor Inhibitory Marine Natural Products
    James Marshall; Fiscal Year: 2004
    ..The main chemical issues to be addressed include the control of stereochemistry by means of chiral organometal chemistry and the design of new and efficient routes to structurally novel natural products. ..