An Asymmetric Total Synthesis of Picrotoxinin through a Mizoroki–Heck Reaction

Abstract

AbstractAn asymmetric total synthesis of picrotoxinin was performed by using a Mizoroki–Heck reaction of an enantioenriched tricyclic lactone with isopropenyl bromide as a key transformation, permitting the highly diastereoselective introduction of the requisite C4-isopropenyl group. After functional-group manipulations, including carbonylation, bromoetherification, epoxidation, and dihydroxylation, picrotoxinin was obtained in a moderate to good yield.