A NOVEL METHOD FOR THE FORMATION OF 2-AZOCANONES BY LACTONE-TO-LACTAMRING CONTRACTION OF 2-OXONANONES

Authors
DERRER S FEEDER N TEAT SJ DAVIES JE HOLMES AB
Citation
S. Derrer et al., A NOVEL METHOD FOR THE FORMATION OF 2-AZOCANONES BY LACTONE-TO-LACTAMRING CONTRACTION OF 2-OXONANONES, Tetrahedron letters, 39(50), 1998, pp. 9309-9312
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
50
Year of publication
1998
Pages
9309 - 9312
Database
ISI
SICI code
0040-4039(1998)39:50<9309:ANMFTF>2.0.ZU;2-J
Abstract
As part of a project evaluating medium-ring lactams as constrained pep tidomimetics, a novel method for the formation of multisubstituted eig ht-membered lactams has been developed. N-Protected 7-amino-8-hydroxyo ctenoic acids were cyclised to give 8-amino-5,6-dehydro-2-oxocanones w hich underwent clean intramolecular O-to-N-acyl (lactone-to-lactam) ri ng contraction to yield 8-hydroxymethyl-6,7-dehydro-2-azocanones, suit able for elaboration to eight-membered lactam dipeptides. (C) 1998 Els evier Science Ltd. All rights reserved.