Total Synthesis of Taxol. 1. Retrosynthesis, Degradation, and Reconstitution

K. C. Nicolaou, P. G. Nantermet, H. Ueno, R. K. Guy, E. A. Couladouros, E. J. Sorensen

Research output: Contribution to journalArticle

193 Scopus citations

Abstract

A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of theD ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.

Original languageEnglish (US)
Pages (from-to)624-633
Number of pages10
JournalJournal of the American Chemical Society
Volume117
Issue number2
DOIs
StatePublished - Jan 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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