Photochemical rearrangement of oxaziridines and nitrones in the hexahydroindole series: a convenient synthetic route to 1-azabicyclo[5.2.0]nonan-2-ones as novel RGD mimetics.
[reaction: see text] Photolysis of oxaziridines a or nitrones b provides a convenient synthetic route to fused bicyclic lactams c adequately substituted on both cycles A and B as scaffolds for mimicking conformationally constrained beta-turn peptides as in the tripeptide RGD signaling motif of fibronectin.
Bourguet
E
E
Laboratoire de Chimie Biomoléculaire et Interactions Biologiques, UMR CNRS 5074, Faculté de Pharmacie, 15, avenue Charles Flahault, 34060 Montpellier Cedex, France.
Baneres
J L
JL
Girard
J P
JP
Parello
J
J
Vidal
J P
JP
Lusinchi
X
X
Declercq
J P
JP
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*; D010777:Photochemistry
D001643:Bridged Bicyclo Compounds; D007211:Indoles; D007769:Lactams; D009589:Nitrogen Oxides; D009842:Oligopeptides; C015388:nitrones; C047981:arginyl-glycyl-aspartic acid