通过多组分反应和酸介导的大环化序列快速合成含糖氨基酸或糖氨基醇的环缩肽。

Rapid synthesis of cyclodepsipeptides containing a sugar amino acid or a sugar amino alcohol by a sequence of a multicomponent reaction and acid-mediated macrocyclization.

作者信息

Bughin Carine, Masson Géraldine, Zhu Jieping

机构信息

Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.

出版信息

J Org Chem. 2007 Mar 2;72(5):1826-9. doi: 10.1021/jo0621874. Epub 2007 Jan 25.

DOI:10.1021/jo0621874

PMID:17253752

Abstract

Cyclodepsipeptides incorporating a sugar amino acid (alcohol) have been synthesized. A three-component reaction of a sugar amino acid (SAA) derivative, an aldehyde, and a dipeptide isonitrile in refluxing methanol afforded the corresponding 5-aminooxazole which, after saponification, underwent a trifluoroacetic acid promoted macrocyclization to furnish the cyclic sugar amino acids.

摘要

已合成了包含糖氨基酸（醇）的环缩肽。糖氨基酸（SAA）衍生物、醛和二肽异腈在回流甲醇中发生三组分反应，得到相应的5-氨基恶唑，皂化后，在三氟乙酸促进下进行大环化反应，得到环状糖氨基酸。