Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic
Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic
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DOI：
10.1016/j.tet.2008.02.076
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发表时间：
2008-05-05
期刊：
影响因子：
2.1
通讯作者：
Fujii, Nobutaka
中科院分区：
文献类型：
--
作者：
Narumi, Tetsuo;Tomita, Kenji;Fujii, Nobutaka
发展了一种非对映选择性合成高度官能化的（Z）-氟烯烃二肽电子等排体的发散方法。该合成方法的主要特点是通过金属转移反应进行还原/不对称烷基化的一锅法反应，高产率地合成了具有两个立体异构中心的反式酰胺型（Z）-氟代烯烃，具有优异的（Z）-选择性和非对映选择性。还描述了一种含有（Z）-氟烯烃电子等排体的特异性CXCR 4拮抗假肽25的基于Fmoc的实用固相合成。(c)2008爱思唯尔有限公司版权所有。
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.