New asymmetric routes to ajmaline and suaveoline indole alkaloids

被引：9

作者：

Bailey, PD ^{[1
]}

Morgan, KM

Smith, DI

Vernon, JM

机构：

[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland

[2] Sanofi Synthelabo Res, Alnwick NE66 2JH, Northd, England

[3] Univ York, Dept Chem, York YO1 5DD, N Yorkshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 21期

关键词：

D O I：

10.1039/b005694o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tetracyclic advanced intermediates 6, 8 and 9 obtained from L-tryptophan via a cis-selective Pictet-Spengler reaction and a Dieckmann-Thorpe cyclisation are used in a range of new approaches to polycyclic monoterpenoid indole alkaloids such as ajmaline and suaveoline. Structural modifications designed to facilitate a key intermolecular addition to C15 (ajmaline numbering) are described, followed by two intramolecular routes based on the addition of a suitable carbon fragment to a remote nitrogen atom prior to bond formation at C15.

引用

页码：3566 / 3577

页数：12

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