Studies towards the total synthesis of (+)-13-deoxytedanolide: stereoselective synthesis of C1–C9 and C9–C17 fragments

Abstract

A facile and stereoselective synthesis of C1–C9 and C9–C17 fragments of (+)-13-deoxytedanolide and studies towards the synthesis of (+)-13-deoxytedanolide was accomplished in 20 linear steps. The key transformations of fragment 6 are Sharpless asymmetric dihydroxylation and preparation of terminal olefin from primary alcohol utilising organo selenium reaction. The key transformations of fragment 7 are from Sharpless epoxidation and Crimmin’s syn aldol chemistry.