Synthesis of 4-Substituted-3-aminopiperidin-2-ones:  Application to the Synthesis of a Conformationally Constrained Tetrapeptide N-Acetyl-Ser-Asp-Lys-Pro

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)-α,β-unsaturated ester (3) and (b) racemization-free reductive aminatio...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-07, Vol.70 (15), p.5946-5953
Main Authors: Kumar, Sukeerthi, Flamant-Robin, Céline, Wang, Qian, Chiaroni, Angèle, André Sasaki, N
Format: Article
Language:English
Subjects:
Amination
Bridged-Ring Compounds - chemistry
Chemistry
Exact sciences and technology
Lactams - chemistry
Models, Chemical
Oligopeptides - chemical synthesis
Oligopeptides - pharmacology
Organic chemistry
Oxidation-Reduction
Peptides
Piperidones - chemical synthesis
Piperidones - pharmacology
Preparations and properties
Stereoisomerism
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Summary: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)-α,β-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).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050736k