Highly Diastereoselective Construction of Substituted Pyrrolidines: Formal Synthesis of (-)-Bulgecinine

被引：12
|
作者：
Das, Biswanath [1 ]
Kumar, Duddukuri Nandan [1 ]
机构：
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
来源：
SYNLETT | 2011年 / 09期
关键词：
substituted pyrrolidine; (-)-bulgecinine; diastereoselective synthesis; asymmetric epoxidation; endo-mode epoxide opening; BULGE-INDUCING ACTIVITY; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC EPOXIDATION; BACTERIAL METABOLITES; EFFICIENT; BULGECININE; ROUTE; ACID;
D O I：
10.1055/s-0030-1260546
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly diastereoselective synthesis of substituted pyrrolidines has been achieved starting from nonchiral molecule, allyl bromide, or cis-but-2-ene-1,4-diol. The method involves the asymmetric epoxidation and endo-mode epoxide opening with azide nucleophile as the key steps. The method has been applied for the formal synthesis of (-)-bulgecinine.
引用
收藏
页码：1285 / 1287
页数：3
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