New asymmetric route to bridged indole alkaloids: Formal enantiospecific syntheses of (-)-suaveoline, (-)-raumacline and (-)-N-b-methylraumacline

被引：23

作者：

Bailey, PD

Collier, ID

Hollinshead, SP

Moore, MH

Morgan, KM

Smith, DI

Vernon, JM

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

[2] STERLING WINTHROP RES CTR,STERLING WINTHROP PHARMACEUT RES DIV,DEPT CHEM DEV,ALNWICK NE66 2JH,NORTHANTS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 08期

关键词：

D O I：

10.1039/a606081a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The homologous nitrile 13 derived from L-tryptophan,undegoes a modified Pictet-Spengler reaction with methyl propynoate, under conditions of kinetic control, to afford the cis-tetrahydro-beta-carboline 15a (cis: trans = 77:23), After protection, Dieckmann-Thorpe cyclisation to the bridged keto nitrile 20 proceeds in 90% yield, Simple functional group modifications via the alcohol 21a and nitrile 22 (structures confirmed by X-ray crystallography) allow convergence with the tetracyclic alpha,beta-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.

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页码：1209 / 1214

页数：6

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