Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton

K. C. Nicolaou, Z. Yang, J. J. Liu, P. G. Nantermet, C. F. Claiborne, J. Renaud, R. K. Guy, K. Shibayama

Research output: Contribution to journalArticlepeer-review

178 Scopus citations

Abstract

The synthesis of Taxol's ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,C10-diol (±)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.

Original languageEnglish
Pages (from-to)645-652
Number of pages8
JournalJournal of the American Chemical Society
Volume117
Issue number2
DOIs
StatePublished - Jan 1995

ASJC Scopus subject areas

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

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