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
收藏
页码：4439 / 4443
页数：5
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