title: Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues.
abstract: Pawhuskin A is a prenylated stilbene that functions as an antagonist of the kappa opioid receptor. Analogues of this natural product bearing different placements of the prenyl group in the A-ring have shown selectivity for either the kappa or the delta receptors subtypes. This differential activity has drawn attention to regiospecific preparation of the C-2, C-5, and C-6 prenylated A-ring regioisomers. Through halogen metal exchange, advanced intermediates representing each of these regioisomers have been prepared, and the new C-6 intermediate has been converted to a new analogue of the natural stilbene.
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: Kevyn D
authors.initials: KD
authors.lastname: Gardner
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D010636:Phenols / Q000737:chemistry*; D017465:Receptors, Opioid, delta / Q000737:chemistry*; D017473:Receptors, Opioid, kappa / Q000037:antagonists & inhibitors / Q000737:chemistry*; D017450:Receptors, Opioid, mu / Q000037:antagonists & inhibitors / Q000737:chemistry*; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010636:Phenols; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D013267:Stilbenes; D013729:Terpenes; C482998:pawhuskin A