Synthetic studies of tedanolide, a marine macrolide displaying potent antitumor activity. Stereoselective synthesis of the C(13)-C(23) segment

摘要

A highly stereoselective synthesis of the C(13)-C(23) segment of tedanolide (1), an 18-membered macrolide isolated from the Caribbean sponge Tedania ignis, displaying significant cytotoxicity against KB and PS tumor cell lines, is described which involves two stereoselective epoxidations of regioisomeric trisubstituted double bonds and a stereospecific S(N)2′ methylation reaction of a trans-γ,δ-epoxy-cis-α,6-unsaturated ester as the key steps.