title: Synthesis of the phenanthrene and cyclohepta[a]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes.
abstract: The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
authors.forename: Ming-Chang P
authors.initials: MC
authors.lastname: Yeh
authors.forename: Ming-Nan
authors.initials: MN
authors.lastname: Lin
authors.forename: Yi-Shiang
authors.initials: YS
authors.lastname: Chou
authors.forename: Tern-Chi
authors.initials: TC
authors.lastname: Lin
authors.forename: Li-Yu
authors.initials: LY
authors.lastname: Tseng
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003508:Cycloheptanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003508:Cycloheptanes; D009281:Naphthalenes; D010616:Phenanthrenes; C031721:naphthalene; C031181:phenanthrene; D006046:Gold