FACILE SYNTHESES AND REARRANGEMENTS OF PEPTIDE DERIVED BETA-LACTAMS

被引：13

作者：

FAROUZ, F ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 28期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)92692-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective aldol condensation of a 4,5-diphenyl-oxazolin-2-one (Ox) glycine provided alpha-amino-beta-hydroxy acid 4, which, after coupling with phenylglycine derivatives, was directly cyclized to beta-lactams. Ozonolysis cleaved both the Ox and isopropylidene groups and initiated a Chapman rearrangement to the corresponding alpha-benzamido-beta-acyl-2-azetidinone 8. Subsequent reduction induced a diastereoselective rearrangement to the corresponding gamma-lactone 13.

引用

页码：3305 / 3308

页数：4

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