Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin

Abstract

The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1–C9 segment 4 was prepared from ( R)-pantolactone, and the C10–C17 segment 14 was synthesized from ( R)-glycidyl trityl ether. The Nozaki–Hiyama–Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon ( 3) of aurisides by construction of the 14-membered lactone and bromine-substituted conjugated diene. The glycosylation reaction of the aglycon provided aurisides A and B.