SYNTHESIS OF E-ALKENE AND Z-ALKENE DIPEPTIDE ISOSTERES

被引：38

作者：

BOHNSTEDT, AC ^{[1
]}

PRASAD, JVNV ^{[1
]}

RICH, DH ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,1101 UNIV AVE,MADISON,WI 53706

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)73956-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of MeLeu-Leu and MeLeu-D-Leu alkene dipeptide isosteres are described. Isosteres with an E-alkene bond were synthesized stereoselectively by employing the [2, 3] Wittig rearrangement to control double bond geometry and C-2 configuration. Z-Alkene isosteres were obtained as an easily separable mixture of diastereomers via alkylation of a Z-alkene MeLeu-Gly isostere that was obtained using a Z-selective Wittig reaction as the key step. All isosteres are isolated with high stereochemical purity.

引用

页码：5217 / 5220

页数：4

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