TITANIUM(III)-MEDIATED SYNTHESIS OF A 1,2,3-TRICARBONYL MOIETY FROM AN ALPHA-OXIMIDO-BETA-KETO ESTER - APPLICATION TO THE SYNTHESIS OF THE CARBACEPHEM NUCLEUS

被引：21

作者：

GASPARSKI, CM ^{[1
]}

GHOSH, A ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 13期

关键词：

D O I：

10.1021/jo00039a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure for the conversion of alpha-oximido-beta-keto esters into vicinal tricarbonyl moieties by TiCl3 in aqueous, buffered (pH 5) conditions with acetone cosolvent was demonstrated. As applied to N-hydroxy beta-lactam 17, which contained an alpha-oximido-beta-keto ester side chain, these combined reductive and hydrolytic conditions effected simultaneous tricarbonyl formation and beta-lactam N-O bond reduction. Vicinal tricarbonyl-containing N-unsubstituted beta-lactam 18 was a direct precursor to semifunctionalized carbacephem 1.

引用

页码：3546 / 3550

页数：5

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