仿生全合成 (-)-靛玉红 A。

Biomimetic total synthesis of (-)-isatisine A.

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, PR China.

出版信息

Org Lett. 2012 Mar 16;14(6):1624-7. doi: 10.1021/ol300379g. Epub 2012 Feb 28.

DOI:10.1021/ol300379g

PMID:22372625

Abstract

The biomimetic total synthesis of (-)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in 8 steps from indole and 4,6-O-isopropylidene-protected glucal. The synthesis features a convergent synthetic strategy which relies on nucleophilic addition and a biomimetic benzilic ester rearrangement as key reactions.

摘要

（-）-靛红 A 是一种具有前所未有的稠合四环骨架的新型生物碱，其仿生全合成工作已从吲哚和 4,6-O-亚异丙基保护的葡萄糖醛酸出发，经 8 步反应完成。该合成采用了依赖于亲核加成和仿生苯甲酰酯重排的关键反应的汇聚合成策略。