(R)-2-甲基-7-炔-辛酸的合成

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%.

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

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%.