基于[2,3]-维蒂希重排和闭环烯烃复分解反应合成西加毒素3C的EF环。

Synthesis of the EF-ring of ciguatoxin 3C based on the [2,3]-Wittig rearrangement and ring-closing olefin metathesis.

作者信息

Goto Akiyoshi, Fujiwara Kenshu, Kawai Ayako, Kawai Hidetoshi, Suzuki Takanori

机构信息

Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

出版信息

Org Lett. 2007 Dec 20;9(26):5373-6. doi: 10.1021/ol702231j. Epub 2007 Dec 4.

DOI:10.1021/ol702231j

PMID:18052179

Abstract

The EF-ring segment of ciguatoxin 3C, a causative toxin of ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O-C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement for the construction of the anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis for the F-ring formation.

摘要

雪卡毒素3C（雪卡鱼中毒的致病毒素）的EF环片段通过三个主要步骤合成：用于连接C20O-C27键的1,4-加成反应、用于构建反式-2-羟烷基醚部分的手性转移反式选择性[2,3]-维蒂希重排反应以及用于形成F环的闭环烯烃复分解反应。