A SHORT STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES

被引：25

作者：

JONES, DM ^{[1
]}

NILSSON, B ^{[1
]}

SZELKE, M ^{[1
]}

机构：

[1] FERRING AB,S-20061 MALMO,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.

引用

页码：2286 / 2290

页数：5

共 37 条

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