title: Evolution of natural product scaffolds by acyl- and arylnitroso hetero-diels-alder reactions: new chemistry on piperine.
abstract: Piperine, a natural product containing a conjugated diene, was reacted with polymer-supported acyl- and arylnitroso dienophiles. The reactions with arylnitroso dienophiles were also carried out in solution. The oxazine rings formed by the corresponding hetero-Diels-Alder reactions were further transformed and novel acyclic as well as heterocyclic derivatives including pyrroles and quinoxalinones were prepared.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA. vkrchnak@nd.edu
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchnák
authors.forename: Katherine R
authors.initials: KR
authors.lastname: Waring
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Ute
authors.initials: U
authors.lastname: Moellmann
authors.forename: Hans-Martin
authors.initials: HM
authors.lastname: Dahse
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D052117:Benzodioxoles / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D053284:Polyunsaturated Alkamides / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D052117:Benzodioxoles; D001688:Biological Products; D009603:Nitroso Compounds; D010880:Piperidines; D053284:Polyunsaturated Alkamides; C008922:piperine