NEW ASYMMETRIC ROUTE TO BRIDGED INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-SUAVEOLINE, (-)-RAUMACLINE AND (-)-N-B-METHYLRAUMACLINE

被引：16

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,ALNICK NE66 2JH,NORTHD,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 13期

关键词：

D O I：

10.1039/c39940001559

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When the homologated nitrile 11 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, the resulting cis-tetrahydro-beta-carboline 12a is ideally functionalised for cyclisation to the bridged ketonitrile 14; simple functional group modifications via the nitrile 15 (structure 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：1559 / 1560

页数：2

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