Total Synthesis of Taxol . 1

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 the D ring and side chain. Degradative studies conf i ied the viability of certain crucial manipulations including oxidation of the C13 position (35 3) and regioselective introduction of the C I-hydroxyl, CZbenzoyloxy moiety (29 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.