高等学校化学学报

高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (8): 1463.

• 研究论文 • 上一篇    下一篇

(R)-2-甲基-7-炔-辛酸的合成

陈宏亮1, 冯亚青1, 许正双2, 刘新刚1   

  1. 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
  • 收稿日期:2004-08-11 出版日期:2005-08-10 发布日期:2005-08-10
  • 通讯作者: 冯亚青(1957年出生),女,教授,博士生导师,从事有机合成化学研究.E-mail:yqfeng@tju.edu.cn E-mail:yqfeng@tju.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20376059)资助.

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

CHEN Hong-Liang1, FENG Ya-Qing1, XU Zheng-Shuang2, LIU Xin-Gang1   

  1. 1. School of Chemical Engineering, Tianjin University, Tianjin 300072, China;
    2. College of Life Science, Peking University Shenzhen School of Graduate, Shenzhen 518055, China
  • Received:2004-08-11 Online:2005-08-10 Published:2005-08-10

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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

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%.

Key words: (R)-2-methyl-7-octynoic acid, Unsymmetrical alkylation, Ohira-Bestmann reagent

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