鸭脚树叶碱的对映选择性全合成。

Enantioselective total synthesis of aspidophytine.

作者信息

Sumi Shinjiro, Matsumoto Koji, Tokuyama Hidetoshi, Fukuyama Tohru

机构信息

Graduate School of Pharmaceutical Sciences, The University of Tokyo, and PRESTO, JST, 7-3-1 Hongo, Bunkyo-ku, Tokyo113-0033, Japan.

出版信息

Org Lett. 2003 May 29;5(11):1891-3. doi: 10.1021/ol034445e.

DOI:10.1021/ol034445e

PMID:12762679

Abstract

[structure: see text] An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.

摘要

[结构：见正文] 描述了一种对映选择性全合成蛇根碱的方法。带有顺式烯烃取代基的吲哚片段通过2-烯基苯基异氰化物的自由基环化，然后将生成的2-碘吲哚衍生物与官能化乙炔单元进行Sonogashira偶联，得以高效制备。在形成11元环胺后，构建了阿朴菲骨架和内酯环，从而完成全合成。