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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (23): 2158-2162. 上一篇    下一篇

研究论文

5-甲基-[(2E,6E)-3,7,11-三甲基-9-氧代十二碳二烯]苯醌和氢醌的首次全合成

李春红, 达世俊, 陈雪松, 周广连, 谢志翔, 李瀛   

  1. 兰州大学功能有机分子化学国家重点实验室, 有机化学研究所, 兰州, 730000
  • 投稿日期:2005-05-13 修回日期:2005-07-21 发布日期:2014-02-14
  • 通讯作者: liying@lzu.edu.cn
  • 作者简介:李瀛,E-mail:liying@lzu.edu.cn;Fax:0931-8913103.
  • 基金资助:

    国家自然科学基金(No.20272020)资助项目.

First Total Synthesis of 5-Methyl-2-(2E,6E-3,7,11-trimethyl-2,6-dodecadien-9-only)benzo-1,4-quinone and the Corresponding Hydroquinone

LI Chun-Hong, DA Shi-Jun, CHEN Xue-Song, ZHOU Guang-Lian, XIE Zhi-Xiang, LI Ying   

  1. State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000
  • Received:2005-05-13 Revised:2005-07-21 Published:2014-02-14

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以2-甲基对苯二酚和香叶基溴为起始原料,经过酚羟基保护,溴代,Li2CuCl4催化的芳基溴与Grignard试剂的偶联以及Julia偶联等一系列反应,完成了裸鳃亚动物的代谢产物,5-甲基-[(2E,6E)-3,7,11-三甲基-9-氧代十二碳二烯]苯醌(1)和氢醌(2)的首次全合成,将1用NaBH4还原,得到(±)-3,(±)-3也是此类天然产物之一.

关键词: 裸鳃亚动物代谢物, 全合成, Li2CuCl4催化偶联, Julia偶联

First total synthesis of triprenylquinones and hydroquinones isolated from endemic nudibranch Leminda millecra, two naturally occurring compounds 5-methyl-2-(2E,6E-3,7,11-trimethyl-2,6-dodecadien-9- onyl)benzo-1,4-quinone (1) and 5-methyl-2-(2E,6E-3,7,11-trimethyl-2,6-dodecadien-9-onyl)-1,4-hydroquinone (2) has been achieved from cheap and available 2-methylhydroquinone (4) and geranyl bromide, involving protection of phenol, bromination, coupling reaction of arylbromide with Grignard reagent catalyzed by Li2CuCl4, Julia coupling, etc. Reduction of 1 with NaBH4, gave one of this kind of natural products, 5-methyl-2-(2E,6E-9-hydroxy-3,7,11-trimethyl-2,6-dodecadienyl)-1,4-hydroquinone (±)-3.

Key words: endemic nudibranch Leminda millecra, total synthesis, catalytic coupling of Li2CuCl4, Julia coupling