Synthesis of cyclopeptide alkaloids by cyclooligomerization of dipeptidyl oxazolines

被引：43

作者：

Wipf, P ^{[1
]}

Miller, CP ^{[1
]}

Grant, CM ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 46期

基金：

美国国家卫生研究院;

关键词：

cyclooligomerization; stereochemistry; cyclopeptide;

D O I：

10.1016/S0040-4020(00)00767-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclodehydration of Cbz-valylthreonine methyl esters with Burgess reagent provides access to cis- and trans-oxazoline segments for cyclooligomerization reactions. The ratio of 12-, 18-, 24-, and larger-ring macrocycles obtained in this process is kinetically controlled and dependent on the relative stereochemistry of the backbone or-carbons. A network of bifurcated hydrogen bonds rigidifies the peptidyl oxazoline strand and positions the valine side chains in either pseudoaxial or pseudoequatorial orientations. In the former case, transannular strain prevents the formation of 12-membered cyclopeptide alkaloids. Several X-ray structures illustrate the conformational preferences in this family of marine natural product analogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9143 / 9150

页数：8

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