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A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics

✍ Scribed by Xiaojun Zhang; Wen Jiang; Aaron C. Schmitt

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 60 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00909-1

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✦ Synopsis

Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH 2 Cl 2 generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6,5 or 7,5-bicyclic lactam.

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