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  • Title: Evolution of natural product scaffolds by acyl- and arylnitroso hetero-diels-alder reactions: new chemistry on piperine.
    Author: Krchnák V, Waring KR, Noll BC, Moellmann U, Dahse HM, Miller MJ.
    Journal: J Org Chem; 2008 Jun 20; 73(12):4559-67. PubMed ID: 18489157.
    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.
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