Conjugate Addition of 2-Acetylindole Enolates to Unsaturated Oxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic Ring System of Ervitsine

被引：6
作者：
Amat, Mercedes [1 ,2 ]
Checa, Begona [1 ,2 ]
Llor, Nuria [1 ,2 ]
Perez, Maria [1 ,2 ]
Bosch, Joan [1 ,2 ]
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Univ Barcelona, Inst Biomed IBUB, E-08028 Barcelona, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 05期
关键词：
Alkaloids; Nitrogen heterocycles; Lactams; Asymmetric synthesis; Cyclization; Michael addition; RACEMIC BICYCLIC LACTAMS; SYNTHETIC ROUTE; DELTA-LACTAMS; ALKALOIDS; STRYCHNOS; ASPIDOSPERMA; ENTRY;
D O I：
10.1002/ejoc.201001020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The stereochemical outcomes of the conjugate addition reactions of 2-acetylindole enolates to the unsaturated phenylglycinol-derived oxazolopiperidone lactams 1a-f have been studied. After reduction of the 2-acylindole carbonyl group, the Michael adduct cis-6 underwent a Lewis acid-promoted intramolecular alpha-amidoalkylation, leading enantioselectively to the tetracyclic ring system of the indole alkaloid ervitsine.
引用
收藏
页码：898 / 907
页数：10
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