title: Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry.
abstract: The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 0200, Australia.
authors: Aymeric
authors: A
authors: Cervi
authors: Paul
authors: P
authors: Aillard
authors: Nourallah
authors: N
authors: Hazeri
authors: Laurent
authors: L
authors: Petit
authors: Christina L L
authors: CL
authors: Chai
authors: Anthony C
authors: AC
authors: Willis
authors: Martin G
authors: MG
authors: Banwell
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold; D006900:Hydroxylation; D008730:Methoxsalen / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena
chemical_list: D001688:Biological Products; D003374:Coumarins; D006046:Gold; C030123:coumarin; C105671:fraxetin; C039409:pimpinellin; D008730:Methoxsalen