Studies towards the synthesis of the C(8)-C(15) fragment of tedanolide

Abstract

Tedanolide is a 18-membered macrolide of marine origin which displays antitumor activity and presents a synthetic challenge. To date, the total synthesis of tedanolide has not been reported however the synthesis of 13-deoxytedanolide, another closely related macrolide isolated from a different sea sponge, was recently accomplished. Progress towards the synthesis of tedanolide is described with specific attention given to the synthesis of the C(8)-C(15) portion of the molecule. The approach involves the use of rigid bicyclic ring systems to control the stereocenters found in the natural product. The approach contained herein has not yet led to the total synthesis of tedanolide but has led to a precursor of the 18-membered ring.