Total synthesis of panaxydol and its stereoisomers as potential anticancer agents

An efficient total synthesis of natural panaxydol 1a and its seven stereoisomers 1b – h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols . Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3 S ,9 R ,10 S )-panaxydol 1e showed a particularly promising cytotoxic effect.