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Catalytic antibody route to the naturally occurring epothilones: Total synthesis of epothilones a-f

Academic Article
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Overview

authors

  • Sinha, Subhash
  • Sun, J.
  • Miller, G. P.
  • Wartmann, M.
  • Lerner, Richard

publication date

  • April 2001

journal

  • Chemistry-a European Journal  Journal

abstract

  • Naturally occurring epothilones have been synthesized starting from enantiomerically pure aldol compounds 9-11, which were obtained by antibody catalysis. Aldolase antibody 38C2 catalyzed the resolution of (+/-)-9 by enantioselective retro-aldol reaction to afford 9 in 90% ee at 50 % conversion. Compounds 10 and 11 were obtained in more than 99% ee at 50% conversion by resolution of their racemic mixtures using newly developed aldolase antibodies 84G3, 85H6 or 93F3. Compounds 9, 10 and 11 were resolved in multigram quantities and then converted to the epothilones by metathesis processes, which were catalyzed by Grubbs' catalysts.

subject areas

  • Anti-Bacterial Agents
  • Antibiotics, Antineoplastic
  • Antibodies, Catalytic
  • Antineoplastic Agents
  • Epothilones
  • Epoxy Compounds
  • Fructose-Bisphosphate Aldolase
  • Haptens
  • Macrolides
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Myxococcales
  • Stereoisomerism
  • Thiazoles
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Research

keywords

  • antibodies
  • antitumor agents
  • chiral resolution
  • epothilones
  • retro-aldol reactions
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Identity

International Standard Serial Number (ISSN)

  • 0947-6539

Digital Object Identifier (DOI)

  • 10.1002/1521-3765(20010417)7:8<1691::aid-chem16910>3.0.co;2-9

PubMed ID

  • 11349910
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Additional Document Info

start page

  • 1691

end page

  • 1702

volume

  • 7

issue

  • 8

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