Ring Closing Metathesis of Unsaturated Amides as a Route to Short and Medium-Sized Unsaturated Lactams and to Ethylenic Pseudopeptides

Giang Vo-Thanh; Valérie Boucard; Hélène Sauriat-Dorizon; François Guibé

doi:10.1055/s-2001-9705

Synlett 2001; 2001(1): 0037-0040
DOI: 10.1055/s-2001-9705

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Ring Closing Metathesis of Unsaturated Amides as a Route to Short and Medium-Sized Unsaturated Lactams and to Ethylenic Pseudopeptides

Giang Vo-Thanh^* , Valérie Boucard, Hélène Sauriat-Dorizon, François Guibé

^*Institut de Chimie Moléculaire d'Orsay, Laboratoire de Catalyse Moléculaire, UPRESA-8075, Bât. 420, Université Paris-Sud, F-91405 Orsay, France; Fax +33(1)69 15 46 80; E-mail: fraguibe@icmo.u-psud.fr

Abstract

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Five- to eight-membered unsaturated lactams have been obtained through ring-closing metathesis of unsaturated amides of various chain lengths and substitution patterns. The obtention of nine-membered unsaturated lactams by the same procedure met only with limited success. Also described in this Letter is the obtention of the Z-ethylenic pseudopeptidic analog of l-Phe-l-Phe through hydrolytic ring opening of (3R,6S)-3,6-dibenzyl-3,6-dihydro-2-pyridone obtained by RCM.

amides - lactams - metathesis - peptides - ring closure

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