title: Total synthesis of (-)-acetylaranotin.
abstract: The key step in this total synthesis of (-)-acetylaranotin is the efficient formation of the characteristic dihydrooxepine ring from cyclohexenone through an unusual vinylogous Rubottom oxidation and a regioselective Baeyer-Villiger oxidation. (-)-Acetylaranotin is obtained in 22 steps from commercially available L-Cbz-tyrosine (Cbz=benzyloxycarbonyl).
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, Sendai, Japan.
authors.forename: Hideto
authors.initials: H
authors.lastname: Fujiwara
authors.forename: Taichi
authors.initials: T
authors.lastname: Kurogi
authors.forename: Shun
authors.initials: S
authors.lastname: Okaya
authors.forename: Kentaro
authors.initials: K
authors.lastname: Okano
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
mesh_terms: D053138:Cyclohexenes / Q000737:chemistry; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; D010082:Oxepins; D010879:Piperazines; C052568:cyclohexene; D000077489:Piperazine; C006370:acetylaranotin