Journal of Organic Chemistry p. 46 - 50 (1986)
Update date:2022-08-04
Topics:
Denis, Jean-Noel
Greene, Andrew E.
Serra, A. Aarao
Luche, Marie-Jacqueline
An asymmetric epoxidation (70-80percent ee) and a highly regioselective epoxide cleavage have been used as the key reactions in the synthesis of the taxol side chain methyl ester (2; <*>95percent ee, 23percent overall yield from phenylacetylene.Transesterifications of 2 (in four steps) have been effected and are exemplified with (-)-isopinocampheol (8), 1,2;3,4-di-O-isopropylidene-D-galactopyranose (9), and methyl gibberellate (10).
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