Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid

被引：53

作者：

Baldwin, JE ^{[1
]}

Fryer, AM ^{[1
]}

Pritchard, GJ ^{[1
]}

机构：

[1] Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 08期

关键词：

D O I：

10.1021/jo000846l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of new C-4 heteroaromatic acromelic acid analogues has been synthesized in a parallel fashion from (-)-alpha -kainic acid 1. Protection of the amine and carboxylate groups of 1 followed by ozonolysis gave methyl ketone 8. A silyl enol ether 9, generated regiospecifically from the methyl ketone 8 using "kinetic" conditions, was brominated in situ with phenyltrimethylammonium perbromide to give the key alpha -bromo ketone 10. Parallel cyclization reactions of bromo ketone 10 with thioamides and thioureas were then performed. The aromatic heterocyclic derivatives 11a-d and 19 produced were deprotected to give the new kainoid amino acids 6a-d and 25 in excellent yield. Compounds 6a and sc show strong binding to the kainate receptor. Reaction of 10 with alternative condensing agents was also briefly investigated.

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页码：2588 / 2596

页数：9

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