Stereoselective synthesis of a chiral synthon, 2,2,5-trisubstituted tetrahydropyran, based on simultaneous 1,3- and 1,6-asymmetric induction via nucleophilic acetal cleavage reaction of the bicyclic acetal: a total synthesis of (-)-malyngolide

Abstract

A chiral 2,2,5-trisubstituted tetrahydropyran is synthesised efficiently via facial and group selective nucleophilic acetal cleavage reaction of a bicyclic acetal, wherein simultaneous 1,3- and 1,6-asymmetric induction from a sulfinyl chirality is accomplished with high diastereoselectivity; this chiral synthon is successfully applied to a total synthesis of (-)-malyngolide.