Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic

被引：47

作者：

Narumi, Tetsuo ^{[1
]}

Tomita, Kenji ^{[1
]}

Inokuchi, Eriko ^{[1
]}

Kobayashi, Kazuya ^{[1
]}

Oishi, Shinya ^{[1
]}

Ohno, Hiroaki ^{[1
]}

Fujii, Nobutaka ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 19期

关键词：

fluoroalkene; peptide isosteres; transmetalation; CXCR4; antagonist;

D O I：

10.1016/j.tet.2008.02.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective and divergent method for synthesis of a highly functionalized (Z)-fluoroalkene dipeptide isosteres has been developed. The key feature of this synthetic method is an efficient one-pot reaction involving reduction/asymmetric alkylation via transmetalation, which produces trans-amide type (Z)-fluoroalkenes flanking two stereogenic centers in high yields, with excellent (Z)-selectivity and diastereoselectivity. Practical Fmoc-based solid-phase synthesis of a specific CXCR4 antagonistic pseudopeptide, 25 containing (Z)-fluoroalkene isostere is also described. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4332 / 4346

页数：15