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(R)-2-甲基-7-炔-辛酸的合成
引用本文:陈宏亮,冯亚青,许正双,刘新刚. (R)-2-甲基-7-炔-辛酸的合成[J]. 高等学校化学学报, 2005, 26(8): 1463-1466
作者姓名:陈宏亮  冯亚青  许正双  刘新刚
作者单位: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
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%.

关 键 词:(R)-2-甲基-7-炔-辛酸  不对称烷基化反应  Ohira-Bestmann试剂  
文章编号:0251-0790(2005)08-1463-04
收稿时间:2004-08-11
修稿时间:2004-08-11

Synthesis of (R)-2-Methyl-7-octynoic Acid
CHEN Hong-liang,FENG Ya-Qing,XU Zheng-Shuang,LIU Xin-Gang. Synthesis of (R)-2-Methyl-7-octynoic Acid[J]. Chemical Research In Chinese Universities, 2005, 26(8): 1463-1466
Authors:CHEN Hong-liang  FENG Ya-Qing  XU Zheng-Shuang  LIU Xin-Gang
Affiliation:1. School of Chemical Engineering, Tianjin University, Tianjin 300072, China;2. College of Life Science, Peking University Shenzhen School of Graduate, Shenzhen 518055, China
Abstract: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%.
Keywords:(R)-2-methyl-7-octynoic acid  Unsymmetrical alkylation  Ohira-Bestmann reagent
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