title: Intramolecular dehydro-Diels-Alder reaction affords selective entry to arylnaphthalene or aryldihydronaphthalene lignans.
abstract: Intramolecular dehydro-Diels-Alder (DDA) reactions are performed affording arylnaphthalene or aryldihydronaphthalene lactones selectively as determined by choice of reaction solvent. This constitutes the first report of an entirely selective formation of arylnaphthalene lactones utilizing DDA reactions of styrene-ynes. The synthetic utility of the DDA reaction is demonstrated by the synthesis of taiwanin C, retrohelioxanthin, justicidin B, isojusticidin B, and their dihydronaphthalene derivatives. Computational methods for chemical shift assignment are presented that allow for regioisomeric lignans to be distinguished.
authors: Department of Chemistry, University of Pittsburgh , 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.
authors: Laura S
authors: LS
authors: Kocsis
authors: Kay M
authors: KM
authors: Brummond
mesh_terms: D061565:Cycloaddition Reaction; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014970:Xanthines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D007783:Lactones; D017705:Lignans; D009281:Naphthalenes; D014970:Xanthines; C467766:taiwanin C