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  

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

作　　者：李春红[1] 达世俊[1] 陈雪松[1] 周广连[1] 谢志翔[1] 李瀛[1] 

机构地区：[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

出　　处：《化学学报》2005年第23期2158-2162,共5页Acta Chimica Sinica

基　　金：国家自然科学基金(No.20272020)资助项目.

摘　　要：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,Li_2CuCl_4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.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 Li2CuC14, 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.

关 键 词：裸鳃亚动物代谢物 全合成 Li2CuCl4催化偶联 Julia 偶联 

分 类 号：O621.3[理学—有机化学]