On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB: A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

Shawn J. Stachel, Mark D. Chappell, Chul Bom Lee, Samuel J. Danishefsky, Ting Chao Chou, Lifeng He, Susan B. Horwitz

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(Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.

Original languageEnglish (US)
Pages (from-to)1637-1639
Number of pages3
JournalOrganic Letters
Issue number11
Publication statusPublished - Jun 1 2000


ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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