Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (-)-Lyconadin C

被引：33
|
作者：
Cheng, Xiayun [1 ]
Waters, Stephen P. [1 ]
机构：
[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 16期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
LYCOPODIUM ALKALOIDS; VINYL ISOCYANATES; REDUCTIVE AMINATION; CONVENIENT REAGENT; CARBONYL-COMPOUNDS; CONSTRUCTION; 2-PYRIDONES; KETONES; LITHIODIAZOACETATE; CYCLIZATION;
D O I：
10.1021/ol401954f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6 pi-electrocyclization to fashion the 2-pyridone system of lyconadin C.
引用
收藏
页码：4226 / 4229
页数：4
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