SYNTHESIS OF A 5-METHYLENE ANALOG OF 5-ENOLPYRUVYLSHIKIMIC ACID

被引：5

作者：

CAMPBELL, MM ^{[1
]}

RABIASZ, HS ^{[1
]}

SAINSBURY, M ^{[1
]}

SEARLE, PA ^{[1
]}

DAVIES, GM ^{[1
]}

机构：

[1] ICI PLC,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)85625-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (+/-)-3-(1-carboxy-3alpha,4alpha-dihydroxycyclohex-1-en-5beta-yl)-2-methylidenepropionic acid, a methylene analogue of 5-enolpyruvylshikimic acid, from methyl 3alpha,4alpha-isopropylidene-5beta-iodomethylcyclohex-1-ene-1-carboxylate is described.The starting compound is obtained from (+/-)-methyl homogabaculate. In addition, both enantiomers of methyl homogabacuate have been synthesised from a Diels-Alder cycloaddition of 1-(t)butoxycarbonyl-1,2-dihydropyridine and the N-acryloyl derivative of Oppolzer's bomane 10,2-sultam.

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页码：9363 / 9372

页数：10

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