Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System

K. C. Nicolaou*, J. J. Liu, Z. Yang, H. Ueno, E. J. Sorensen, C. F. Claiborne, R. K. Guy, C. K. Hwang, M. Nakada, P. G. Nantermet

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

220 Citations (Scopus)

Abstract

A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro—McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A—B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

Original languageEnglish
Pages (from-to)634-644
Number of pages11
JournalJournal of the American Chemical Society
Volume117
Issue number2
DOIs
Publication statusPublished - 1995 Jan
Externally publishedYes

ASJC Scopus subject areas

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

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