Toward the synthesis of brevipolide H

Abstract

A linear diastereoselective synthesis of C1–C12 fragment of brevipolide H is described. The key reactions include Jørgensen’s asymmetric epoxidation, palladium-catalyzed regioselective opening of α,β-unsaturated γ,δ-epoxide, Charette’s modified Simmons–Smith cyclopropanation, anti-selective reduction of cyclopropyl containing α,β-unsaturated ketone, Brown allylation, and ring-closing metathesis reaction.