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

页码：1609 / 1614

页数：6

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