Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: Asymmetric synthesis of (-)-horsfiline

被引：123

作者：

Cravotto, G

Giovenzana, GB

Pilati, T

Sisti, M

Palmisano, G ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim Fis & Matemat, Via Valleggio 11, I-22100 Como, Italy

[2] Univ Turin, Dipartimento Sci & Tecnol Farmaco, I-0125 Turin, Italy

[3] Univ Piemonte Orientale, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy

[4] CNR, Ctr Studio Relaz Struttura & Reattiv Chim, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 25期

关键词：

D O I：

10.1021/jo015854w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular [3+2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrollidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (-)-horsfiline 1, based on chiral auxiliary-directed- pi -face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

引用

页码：8447 / 8453

页数：7

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