Synthesis of axinohydantoins.
A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.
Barrios Sosa
Ana Carolina
AC
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
Yakushijin
Kenichi
K
Horne
David A
DA
D000818:Animals; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D018360:Crystallography, X-Ray; D003500:Cyclization; D006827:Hydantoins / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
D006827:Hydantoins; D011758:Pyrroles