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Synthesis of 4-substituted-3-aminopiperidin-2-ones: application to the synthesis of a conformationally constrained tetrapeptide N-acetyl-Ser-Asp-Lys-Pro.

作者信息

Kumar Sukeerthi, Flamant-Robin Céline, Wang Qian, Chiaroni Angèle, Sasaki N André

机构信息

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

出版信息

J Org Chem. 2005 Jul 22;70(15):5946-53. doi: 10.1021/jo050736k.

DOI:10.1021/jo050736k
PMID:16018690
Abstract

A new and practical synthetic strategy is developed for the synthesis of six-membered lactam-bridged dipeptides, 4-substituted-3-aminopiperidin-2-ones, featuring two key steps: (a) a diastereoselective addition of cuprate to (E)-alpha,beta-unsaturated ester (3) and (b) racemization-free reductive amination. On the basis of this methodology, conformationally constrained tetrapeptide N-acetyl-Ser-Asp-Lys-Pro (AcSDKP) (2) has been successfully synthesized from 3-amino-4-vinylpiperidin-2-one (22).

摘要

相似文献

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Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to gamma-alkoxy-alpha,beta-enoates.
用于预测有机铜酸盐与γ-烷氧基-α,β-烯酸酯共轭加成反应立体化学过程的选择性指导原则及基于还原消除的模型。
J Org Chem. 2006 Mar 31;71(7):2630-40. doi: 10.1021/jo052383v.