Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (7): 1329.

• Articles • Previous Articles     Next Articles

First Asymmetric Synthesis of (7R,10S)-Boivinianin B

XU Bo-Yan1, SONG Na1, LI Wen-Ze2, XIN Zhi-Jun1, LI Ying1*   

  1. 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
    2. Jiuzhou Pharmaceutical Co., Ltd., Taizhou 318000, China
  • Received:2009-01-13 Online:2009-07-10 Published:2009-07-10
  • Contact: LI Ying. E-mail: liying@lzu.edu.cn
  • Supported by:

    国家自然科学基金(批准号: 20672050)资助.

Abstract:

(7R,10S)-Boivinianin B(1), a naturally occurring sesquiterpene which has a synthetically challenging 2,2,5-tri-substituted tetrahydrofuran skeleton, was isolated from Laurencia tristicha and Cipadessa boiviniana. First asymmetric synthesis of the title compound was developed by sharpless asymmetric dihydroxyation to generate a stereocenter which as a chiral pool in the next procedure and an intramolecular iodoetherification to construct the tetrahydrofuran skeleton. The method developed here will be a useful tool for the stereoselective synthesis of 2,2,5-tri-substituted tetrahydrofurans bearing sterically congested benzylic quaternary center.

Key words: Asymmetric synthesis;(7R,10S)-Boivinianin B; Iodoetherification

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