Asymmetric Total Synthesis of 3-Furanoeudesmene, A Metabolitefrom Antarctic Gorgonian and Determination of Its AbsoluteConfiguration

Abstract

The first total synthesis of 3-furanoeudesmene, an eudesmane-type sesquiterpenoid, is reported herein. Starting from the commercially available (＋)-verbenone, the target molecule was achieved stereoselectively over eight steps, with ring closing metathesis and three-step synthesis of furan as the keypoints. The absolute configuration of 3-furanoeudesmene was determined by comparison of the optical rotation value of the synthetic sample with that of the natural product.