SYNTHESIS OF PHENYLALANINE-BASED CYCLIC ACYLATED ENAMINO ESTER DIPEPTIDE ANALOGS - INHIBITORS OF ALPHA-CHYMOTRYPSIN - X-RAY MOLECULAR-STRUCTURE OF (2'S,4'R)-4'-BENZYL-3'-BENZYLOXYCARBONYL-5'-OXO-2'-PHENYLOXAZOLIDIN-4'-YL ACETIC-ACID

被引：12

作者：

ABELL, AD

OLDHAM, MD

TAYLOR, JM

机构：

[1] Department of Chemistry, University of Canterbury, Christchurch

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 07期

关键词：

D O I：

10.1039/p19950000953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of the (S)-phenylalanine-derived syn-oxazolidinone 8 with BrCH(2)CO(2)CHPh(2) gave compound 9, a key precursor to the beta-keto ester 11 and the keto acid phosphorane 17. Compound 17 gave the enolactone 24 on heating and the bromo enolactones 19 and 20 on treatment with bromine and triethylamine. Compounds 11, 19, 20 and 24 were treated with glycine ethyl ester to give the Phe-Gly dipeptide mimics 22, 23 and 26. The enolactone 24 also gave the Phe-Ala mimic 39 and the Phe-Gly-Gly mimic 34.

引用

页码：953 / 961

页数：9

共 32 条

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