title: Platinum-catalyzed synthesis of substituted phenanthrenes from biphenyl propargyl alcohols via a carbene intermediate.
abstract: An efficient synthesis for phenanthrenes via a Pt-carbene intermediate is described. Using Pt as a catalyst, the readily accessible biphenyl propargyl alcohol substrate can be transformed to the vinylphenanthrene system through a cascade involving electrophilic cyclization, dehydration, and 1,2-H migration. The synthetic utility and efficiency of this protocol were demonstrated via the concise total synthesis of antofine.
authors.affiliation: College of Pharmacy, Seoul National University , Seoul 151-742, Korea.
authors.forename: Yongseok
authors.initials: Y
authors.lastname: Kwon
authors.forename: Illan
authors.initials: I
authors.lastname: Kim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D017671:Platinum Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*
chemical_list: D000480:Alkynes; D007211:Indoles; D010616:Phenanthrenes; D010618:Phenanthrolines; D017671:Platinum Compounds; D020005:Propanols; C473343:antofine; C030173:platinum chloride; C030011:carbene; C028255:propargyl alcohol; D008697:Methane