Stereoselective Construction of 2,6-cis-Disubstituted Tetrahydropyrans via Intramolecular Amide Enolate Alkylation: Total Synthesis of (-)-Centrolobine

摘要

A highly stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans was achieved by using an intramolecular amide enolate alkylation with KHMDS. The efficiency and practicality of this methodology was successfully demonstrated in the total synthesis of (-)-centrolobine (1).