(R)-2-甲基-7-炔-辛酸的合成  

Synthesis of (R)-2-Methyl-7-octynoic Acid

作　　者：陈宏亮[1] 冯亚青[1] 许正双[2] 刘新刚[1] 

机构地区：[1]天津大学化工学院,天津300072 [2]北京大学深圳研究生院生命科学与技术学院,深圳518055

出　　处：《高等学校化学学报》2005年第8期1463-1466,共4页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20376059)资助.

摘　　要：以1,5-戊二醇为起始原料,用Evans手性助剂诱导的烷基化反应构造了C-2手性中心,用Ohira-Bestmann试剂制备了末端炔基,通过13步反应,合成了(R)-2-甲基-7-炔-辛酸,总收率为17.1%,e.e.值大于99%.The marine peptides have been a fertile source for new bioactive molecules, and many possess potent activity, across a broad spectrum of targets. Their diversity in both biological activity and in chemical complexity has made these secondary metabolites being the focus of much work in recent years. As a fragment, （R）-2-methyloctanoic acid-7-yne was always found in those nature materials. In this article, （R）-2-methyl-7-octynoic acid was synthesized with pentane-1,5-diol as the start material. Stereogenic carbon（C-2） was obtained through alkylation induced with Evans＇ chiral auxiliary, and alkyne 13 was got by use of Ohira-Bestmann reagent. Through 13-step reactions the target molecule was prepared with over yield of 17.1%, and e.e. beyond 99%.

关 键 词：(R)-2-甲基-7-炔-辛酸 不对称烷基化反应 Ohira-Bestmann试剂 1 5-戊二醇 

分 类 号：O623.612[理学—有机化学]