Taxol Total Synthesis: Preparation of a Chiral Ring a Moiety via Biomimetic Cyclization and Evaluation of a Tandem Nitrile Oxide Strategy for Rings B/C1

L. Alcaraz, J. J. Harnett, C. Mioskowski, T. Le Gall, Dong Soo Shin, J. R. Falck

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

A fully functionalized taxol ring A moiety 7 was efficiently prepared via biomimetic cation-olefm cyclization of chiral geraniol epoxide 2b using SnCl4 in toluene. Fractional crystallization provided endo-3 (50% yield from 2b) that was converted to aldehyde 5 by stereospecific epoxidation, secondary alcohol protection, and PCC oxidation. NaOMe-mediated ring opening secured enal 6. Addition of lithium dith'iane to 6 at low temperature provided 7 as the sole product in good yield. A tandem nitrile oxide cycloaddition strategy for creating the remaining B/C carbocycles as well as key functionality present in both rings was validated, in part, by cyclization of 14 to tricyclic isoxazoline 15.

Original languageEnglish (US)
Pages (from-to)7209-7214
Number of pages6
JournalJournal of Organic Chemistry
Volume60
Issue number22
DOIs
StatePublished - Nov 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

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