有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2157-2161.DOI: 10.6023/cjoc201505001 上一篇    下一篇

研究论文

南极柳珊瑚代谢物3-Furanoeudesmene的立体选择性全合成及绝对构型确定

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 E-mail:chembliu@scu.edu.cn
  • 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).

报道了对桉烷倍半萜天然产物3-furanoeudesmene的首次全合成. 从商品化手性试剂(+)-马鞭烯酮出发, 以关环烯烃复分解反应及三步法呋喃环构建为关键步骤, 总共八步反应实现了目标分子的立体选择性合成. 通过比对合成的目标分子的旋光值与天然产物的旋光值, 确定出天然产物的绝对构型.

关键词: 桉烷, 倍半萜, 呋喃, 全合成, 绝对构型

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