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

Research output: Contribution to journalArticle

213 Scopus citations

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 (US)
Pages (from-to)634-644
Number of pages11
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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    Nicolaou, K. C., Liu, J. J., Yang, Z., Ueno, H., Sorensen, E. J., Claiborne, C. F., Guy, R. K., Hwang, C. K., Nakada, M., & Nantermet, P. G. (1995). Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System. Journal of the American Chemical Society, 117(2), 634-644. https://doi.org/10.1021/ja00107a007