Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach

被引：40

作者：

Catozzi, Nicola ^{[1
]}

Edwards, Michael G. ^{[1
]}

Raw, Steven A. ^{[2
]}

Wasnaire, Pierre ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] AstraZeneca, Proc Res & Dev, Macclesfield SK10 2NA, Cheshire, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; NONSTEROIDAL GROWTH-INHIBITORS; HIGHLY SUBSTITUTED PYRIDINES; BAEYER-VILLIGER OXIDATION; RESPONSIVE SC-115 CELLS; HETEROCYCLIC AZADIENES; EFFICIENT SYNTHESIS; TANDEM OXIDATION; CHIRAL PYRIDINE; COPPER CATALYST;

D O I：

10.1021/jo901761r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

引用

页码：8343 / 8354

页数：12

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