高等学校化学学报

高等学校化学学报 ›› 1994, Vol. 15 ›› Issue (3): 387.

• 论文 • 上一篇    下一篇

经由胂叶立德立体有择合成仿保幼激素──增丝素(ZR-512)及其(2Z,4E)-异构体

刘天麟, 倪赤友, 谢文权, 李正名   

  1. 南开大学元素有机化学研究所, 天津, 300071
  • 收稿日期:1993-04-09 修回日期:1993-09-05 出版日期:1994-03-24 发布日期:1994-03-24
  • 通讯作者: 刘天麟,男,53岁,副教授.
  • 作者简介:刘天麟,男,53岁,副教授.
  • 基金资助:

    国家自然科学基金

Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide

LIU Tian-Lin, NI Chi-You, XIE Wen-Quan, LI Zheng-Ming   

  1. Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071
  • Received:1993-04-09 Revised:1993-09-05 Online:1994-03-24 Published:1994-03-24

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被引次数

2

摘要： 3-甲基-2-丁烯酸乙酯4经SeO2反式氧化、还原、溴化得到关键中间体4-溴-3-甲基-(2E)-丁烯酸乙酯7.7与三苯基胂反应生成季8.二氢香茅醛与8在K)2CO)3-乙醇-微量水的存在下反应,得到(2E,4E)-3,7,11-三甲基-2,4-十二碳二烯酸乙酯1a及其(2Z,4E)-异构体1b,产率74%.该反应具有(4E)-立体选择性,同时C-2双键发生部分构型转化。

关键词: 增丝素(ZR-512), 胂叶立德, 立体选择性, 合成

Abstract: The key intermediate ethyl 4-bromo-3-methyl-( 2E)-butenoate 7 was obtained from ethyl 3-methyl-2-butenoate 4 by a sequence of reactions:trans-oxidation(SeO2), reduction and bromination, Reaction of 7 and triphenylarsine gave the arsonium salt 8.Finally, reaction of 8 and dihydrocitronellal in the presence of K2CO3-C2H5OH-trace H2O afforded hydroprene and its (2Z, 4E)-isomer in yield of 74%.The(4E)-selectivity and the partial inversion of C-2 double bond configuration happened in this reaction.

Key words: Hydroprene, Arsonic Ylide, Stereoselectivity, Synthesis

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