title: Total syntheses of multicaulins via oxidative photocyclization of stilbenes.
abstract: The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
authors.affiliation: Department of Chemistry, Faculty of Sciences, Ataturk University , 25240 Erzurum, Turkey.
authors.forename: Hatice
authors.initials: H
authors.lastname: Seçinti
authors.forename: Serdar
authors.initials: S
authors.lastname: Burmaoğlu
authors.forename: Ramazan
authors.initials: R
authors.lastname: Altundaş
authors.forename: Hasan
authors.initials: H
authors.lastname: Seçen
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013267:Stilbenes / Q000737:chemistry*
chemical_list: C000594574:2,3-dimethylbenzylphosphonium bromide; C000594573:3-isopropyl-4-methoxybenzaldehyde; D001547:Benzaldehydes; D009943:Organophosphorus Compounds; D010616:Phenanthrenes; D013267:Stilbenes; C000594635:multicaulin