Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F. Academic Article uri icon

Overview

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.

publication date

  • April 17, 2001

Research

keywords

  • Anti-Bacterial Agents
  • Antibodies, Catalytic
  • Antineoplastic Agents
  • Epothilones
  • Epoxy Compounds
  • Thiazoles

Identity

Scopus Document Identifier

  • 0035901666

Digital Object Identifier (DOI)

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

PubMed ID

  • 11349910

Additional Document Info

volume

  • 7

issue

  • 8