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 language | English (US) |
---|---|
Pages (from-to) | 7209-7214 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 60 |
Issue number | 22 |
DOIs | |
State | Published - Nov 1 1995 |
ASJC Scopus subject areas
- Organic Chemistry