title: Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers.
abstract: We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo.
authors.forename: Mio
authors.initials: M
authors.lastname: Kubota
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Saito
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
authors.forename: Keiichi
authors.initials: K
authors.lastname: Hirano
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry
chemical_list: D000438:Alcohols; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D004987:Ethers; D010165:Palladium; D006046:Gold