Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2157-2161.DOI: 10.6023/cjoc201505001 Previous Articles     Next Articles



于天姿, 刘波   

  1. 四川大学化学学院 成都 610064
  • 收稿日期:2015-05-01 修回日期:2015-06-01 发布日期:2015-06-04
  • 通讯作者: 刘波
  • 基金资助:

    国家自然科学基金(No. 21172154)资助项目.

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

Yu Tianzi, Liu Bo   

  1. College of Chemistry, Sichuan University, Chengdu 610064
  • Received:2015-05-01 Revised:2015-06-01 Published:2015-06-04
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21172154).

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.

Key words: eudesmane, sesquiterpenoid, furan, total synthesis, absolute configuration