SmI2-mediated hetero-coupling reaction of lactams with aldehydes;: synthesis of indolizidine alkaloids, (-)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

被引：58

作者：

Yoda, H ^{[1
]}

Katoh, H ^{[1
]}

Ujihara, Y ^{[1
]}

Takabe, K ^{[1
]}

机构：

[1] Shizuoka Univ, Fac Engn, Dept Mol Sci, Hamamatsu, Shizuoka 4328561, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 13期

基金：

日本学术振兴会;

关键词：

coupling reaction; samarium(II) diiodide; lactam; indolizidine alkaloid; lentiginosine;

D O I：

10.1016/S0040-4039(01)00214-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2509 / 2512

页数：4

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