Probing the SAR of dEpoB via chemical synthesis: a total synthesis evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

J Org Chem. 2002 Nov 1;67(22):7730-6. doi: 10.1021/jo020180q.

Abstract

A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Disease Progression
  • Epothilones / chemical synthesis*
  • Epothilones / chemistry
  • Epothilones / therapeutic use*
  • Epothilones / toxicity
  • Epoxy Compounds / chemistry
  • Inhibitory Concentration 50
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Structure-Activity Relationship
  • Xenograft Model Antitumor Assays

Substances

  • Epothilones
  • Epoxy Compounds
  • desoxyepothilone B