高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (7): 1329.

• 研究论文 • 上一篇    下一篇

(7R,10S)-Boivinianin B的不对称合成

许柏岩1, 宋娜1, 李文泽2, 辛志君1, 李瀛1   

  1. 1. 兰州大学功能有机分子化学国家重点实验室, 兰州 730000;
    2. 九洲药业股份有限公司, 台州 318000
  • 收稿日期:2009-01-13 出版日期:2009-07-10 发布日期:2009-07-10
  • 通讯作者: 李瀛, 男, 教授, 博士生导师, 主要从事天然产物的全合成研究. E-mail: liying@lzu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 20672050)资助.

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.

摘要:

报道了一种基于Dehydro-α-curcumene(4)为关键中间体, 以Sharpless不对称双羟化反应和碘催化的分子内环化成醚反应为关键步骤, 构建2,2,5位三取代的四氢呋喃骨架的方法, 完成了(7R,10S)-Boivinianin B(1)的不对称合成. 合成路线简捷, 对此类化合物的合成有一定的借鉴意义.

关键词: 不对称合成; (7R, 10S)-Boivinianin B; 碘化成醚反应

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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