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
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.
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页码:5217 / 5220
页数:4
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