Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids

被引：66

作者：

He, Weigang ^{[1
]}

Hu, Jiadong ^{[1
]}

Wang, Pengyan ^{[1
]}

Chen, Le ^{[1
]}

Ji, Kai ^{[1
]}

Yang, Siyu ^{[1
]}

Li, Yin ^{[1
]}

Xie, Zhilong ^{[1
]}

Xie, Weiqing ^{[1
,2
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 14期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; indole alkaloids; Michael addition; oxindoles; synthetic methods; NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; ASYMMETRIC ALLYLIC SUBSTITUTION; AZA-COPE REARRANGEMENTS; RECENT PROGRESS; (+/-)-DEHYDROTUBIFOLINE; (-)-TUBIFOLINE; (+/-)-AKUAMMICINE; SPIROOXINDOLES; CHEMISTRY;

D O I：

10.1002/anie.201800567

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N-dioxide Sc(OTf)(3) catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] was achieved in 10-11 steps.

引用

页码：3806 / 3809

页数：4

共 66 条

[41] Construction of spiro[pyrrolidine-3,3′-oxindoles] -: Recent applications to the synthesis of oxindole alkaloids [J].