Evolution of natural product scaffolds by acyl- and arylnitroso hetero-diels-alder reactions: new chemistry on piperine.
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.
Krchnák
Viktor
V
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA. vkrchnak@nd.edu
Waring
Katherine R
KR
Noll
Bruce C
BC
Moellmann
Ute
U
Dahse
Hans-Martin
HM
Miller
Marvin J
MJ
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*
D000470:Alkaloids; D052117:Benzodioxoles; D001688:Biological Products; D009603:Nitroso Compounds; D010880:Piperidines; D053284:Polyunsaturated Alkamides; C008922:piperine