Reaction of Donor-Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)-Strychnine and the Total Synthesis of (±)-Akuammicine

被引：102

作者：

Feng, Liang-Wen ^{[1
]}

Ren, Hai ^{[1
]}

Xiong, Hu ^{[1
]}

Wang, Pan ^{[1
]}

Wang, Lijia ^{[1
]}

Tang, Yong ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 11期

基金：

中国国家自然科学基金;

关键词：

annulations; cyclobutanes; diastereoselectivity; heterocycles; natural products; ASYMMETRIC TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; 4+2 CYCLOADDITION; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; SUBSTITUTED CYCLOPROPANE; STRATEGY; STRYCHNINE; (+/-)-ASPIDOSPERMIDINE; (+/-)-GONIOMITINE;

D O I：

10.1002/anie.201611734

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ligand-promoted catalytic [4+2] annulation reaction using indole derivatives and donor-acceptor (D-A) cyclobutanes is reported, thus providing an efficient and atom-economical access to versatile cyclohexa-fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94% ee. This novel synthetic method is applied as a general protocol for the total synthesis of (+/-)-akuammicine and the formal total synthesis of (+/-)-strychnine from the same common-core scaffold.

引用

页码：3055 / 3058

页数：4

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