Stereoselective synthesis of the C3–C12 subunit of laulimalide

A stereoselective synthesis of the C3–C12 subunit of the tumor growth inhibitors laulimalide is disclosed. The key steps of the synthesis include asymmetric alkylation using Oppolzer’s protocol and an asymmetric hetero-Diels–Alder reaction using Jacobsen’s catalyst. Substrate controlled diastereoselective Luche reduction followed by Ferrier type reactions are other key steps.