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 journalArticlepeer-review

211 Scopus citations


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
Pages (from-to)624-633
Number of pages10
JournalJournal of the American Chemical Society
Issue number2
StatePublished - Jan 1995

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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