由D-葡糖醛合成sporolide B。

Synthesis of sporiolide B from D-glucal.

作者信息

Chen Qi, Du Yuguo

机构信息

State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, PR China.

出版信息

Carbohydr Res. 2007 Aug 13;342(11):1405-11. doi: 10.1016/j.carres.2007.04.013. Epub 2007 Apr 29.

DOI:10.1016/j.carres.2007.04.013

PMID:17517381

Abstract

A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound.

摘要

以D - 葡萄糖烯为原料，经17步反应，总收率为4.8%，完成了12元环天然大环内酯类化合物孢子内酯B的全合成。通过在手性模板D - 葡萄糖烯上应用Mitsunobu反应，很容易引入孢子内酯B中C - 3和C - 5所需的立体化学构型。山口酯化反应和闭环复分解反应极大地改善了目标化合物的合成路线。