Synthesis of (+)-Lycoricidine by the Application of Oxidative and Regioselective Ring-Opening of Aziridines

被引：47
|
作者：
Yadav, J. S. [1 ]
Satheesh, G. [1 ]
Murthy, Changalvala V. S. R. [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, CSIR, Hyderabad 500007, Andhra Pradesh, India
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 11期
关键词：
STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; BETA-AZIDONATION REACTION; ANTINEOPLASTIC AGENTS; AMARYLLIDACEAE CONSTITUENTS; NARCICLASINE ALKALOIDS; BIOLOGICAL EVALUATION; ENT-LYCORICIDINE; (+)-PANCRATISTATIN; (+)-NARCICLASINE;
D O I：
10.1021/ol100755v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly stereoselective total synthesis of (+)-lycoricidine has been described. The salient features of this synthesis are the one-pot elimination followed by allylation reaction, ring-closing metathesis, stereoselective aziridine formation, Dess-Martin periodinane, and silica gel mediated oxidative ring-opening of aziridine to form alpha,beta-unsaturated ketone (allyl amine) and intramolecular Heck cyclization.
引用
收藏
页码：2544 / 2547
页数：4
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