A CONCISE ENANTIOSELECTIVE SYNTHESIS OF TRANS-OLEFIN DIPEPTIDE ISOSTERES

被引：31
作者：
BERESIS, R [1 ]
PANEK, JS [1 ]
机构：
[1] BOSTON UNIV,METCALF CTR SCI & ENGN,DEPT CHEM,BOSTON,MA 02215
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 08期
关键词：
D O I：
10.1016/S0960-894X(00)80027-X
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A new asymmetric synthesis of trans-olefin dipeptide isosteres is described which utilizes chiral allylsilane based-bond construction methodology involving a Lewis acid promoted electrophilic addition of chiral (E)-crotylsilanes to the formaldehyde equivalent s-trioxane. The reaction results in the simultaneous introduction of a trans double bond and both amino acid side chains with high levels of diastereo- and enantioselection. The derived isostere units were incorporated into tetrapeptides and their inhibitory constants determined against the HIV-1 protease.
引用
收藏
页码：1609 / 1614
页数：6
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