高等学校化学学报

高等学校化学学报 ›› 1995, Vol. 16 ›› Issue (9): 1391.

• 论文 • 上一篇    下一篇

手性亚砜法立体选择性合成手性非洲蔗螟性信息素(+)-Eldanolide

徐章煌1, 黄锦霞1, 李焰1, 陈祖兴1, 高明章2   

  1. 1. 湖北大学化学系, 武汉, 430062;
    2. 西江大学化学系, 肇庆, 526000
  • 收稿日期:1994-09-21 修回日期:1995-02-20 出版日期:1995-09-24 发布日期:1995-09-24
  • 通讯作者: 徐章煌,男,61岁.教授.
  • 作者简介:徐章煌,男,61岁.教授.
  • 基金资助:

    国家自然科学基金

Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide

XU Zhang-Huang1, HUANG Jin-Xia1, LI Yan1, CHEN Zu-Xing1, GAO Ming-Zhang2   

  1. 1. Department of Chemistry Hubei University, Wuhan, 430062;
    2. Department of Chemistry, Xijiang University, Zhaoqing
  • Received:1994-09-21 Revised:1995-02-20 Online:1995-09-24 Published:1995-09-24

PDF (PC)

被引次数

2

摘要： 手性亚砜(+)-R-手性烷基亚砜与巴豆酸甲酯进行不对称Michael加成反应,立体选择性地合成了(+)-Eldanolide,全合成的光学产率约为39%,其顺、反异构体之比为8:92.

关键词: 非洲蔗螟性信息素, 手性亚砜, Michael加成反应

Abstract: In this paper,(+)-Eldanolide,one of the pheromones of the male African sugarcane borer (Eldana Saccharina), was stereoseiectively synthesized by employing Michael addition of (+)-(R )-4-methyl-1-(p-tolysulfinyl)-3-pentene to trans-methyl crotonate, deoxygenation of the sulfoxide group by sodium iodide and trifluoroacetic anhydride,regioselective methylation by trimethyloxonium tetrafluoroborate and stereospecific lactonation by potassium t-butoxide through an SN2 mechanism. The enantiomeric excess of the total synthesis is about 39% e.e.and the ratio of trans-and cis-disubstituted lactones is trans: cis= 92: 8.

Key words: Eldanolide, Chiral sulfoxide, Michael addition

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