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.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
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.
