Liu D G, Wang B, Lin G Q
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
J Org Chem. 2000 Dec 29;65(26):9114-9. doi: 10.1021/jo005612g.
As a new member of the sphingofungin family, sphingofungin F exhibits interesting physiological activities with a structural unit of an alpha-substituted alanine. Described herein is an efficient and convenient stereoselective synthesis of sphingofungin F from L-(+)-tartaric acid, which utilizes Sharpless asymmetric epoxidation of allylic alcohol and Lewis acid-catalyzed intramolecular epoxide-opening reaction with an N-nucleophile, to introduce the other two desired stereogenic centers. Side chain functionality was incorporated into the chiral segment using a Wittig reaction.
作为鞘氨醇菌素家族的新成员，鞘氨醇菌素F以α-取代丙氨酸的结构单元展现出有趣的生理活性。本文描述了一种从L-(+)-酒石酸高效便捷地立体选择性合成鞘氨醇菌素F的方法，该方法利用烯丙醇的夏普莱斯不对称环氧化反应以及路易斯酸催化的与N-亲核试剂的分子内环氧化物开环反应，以引入另外两个所需的立体中心。使用维蒂希反应将侧链官能团引入到手性片段中。
