Epoxide-initiated electrophilic cyclization of azides:: A novel route for the stereloselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D

被引：60

作者：

Reddy, PG ^{[1
]}

Varghese, B ^{[1
]}

Baskaran, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol027563v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel and general method for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide initiated electrophilic cyclization of azides has been developed and applied in the synthesis of (+/-)-indolizidine 167B and 209D with an overall yield of 16.5% and 17.8%, respectively. The efficiency of this methodology is further exemplified in the synthesis of azepine skeleton via tandem cation-olefin-azide cyclization.

引用

页码：583 / 585

页数：3

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