Abstract
A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of theD ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.
Original language | English |
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Pages (from-to) | 624-633 |
Number of pages | 10 |
Journal | Journal of the American Chemical Society |
Volume | 117 |
Issue number | 2 |
DOIs | |
State | Published - Jan 1995 |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry