Dearomatization of Indole via Intramolecular [3+2] Cycloaddition: Access to the Pentacyclic Skeleton of Strychons Alkaloids

被引：17

作者：

Wang, Zhengshen ^{[1
]}

Chen, Luxin ^{[1
]}

Yao, Yuan ^{[1
]}

Liu, Zhigang ^{[1
]}

Gao, Jin-Ming ^{[1
]}

She, Xuegong ^{[2
]}

Zheng, Huaiji ^{[1
,3
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 3 Taicheng Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 South Tianshui Rd, Lanzhou 730000, Gansu, Peoples R China

[3] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

基金：

中国国家自然科学基金;

关键词：

GOLD(I)-CATALYZED TANDEM 1,2-ACYLOXY; CATALYTIC CARBOPHILIC ACTIVATION; PROPARGYLIC ESTERS; MOLECULAR COMPLEXITY; EFFICIENT SYNTHESIS; EXPEDITIOUS ACCESS; PLATINUM CATALYSIS; CASCADE REACTIONS; GOLD CATALYSIS; CYCLIZATION;

D O I：

10.1021/acs.orglett.8b01720

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to build various multi substituted polycyclic indoline-annulated normal to medium size rings through dearomatization of indole via a tandem 1,2-acyloxy migration/intramolecular [3 + 2] cycloaddition process is described. The pentacyclic skeleton of strychnine could be synthesized via this tandem cycloaddition and a further Mannich reaction. This approach would provide a novel strategy to the synthesis of strychons alkaloids.

引用

页码：4439 / 4443

页数：5

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