title: A new artificial cyclase for polyprenoids: enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11'-deoxytaondiol methyl ether.
abstract: This paper describes a new artificial cyclase, optically pure 3-o-fluorobenzyloxy-2-hydroxy-2'-(p-methoxybemzyl)-1,1'-binaphthyl.SnCl4, which is effective for the enantioselective cyclization of 2-(polyprenyl)phenol derivatives to afford polycyclic terpenoids bearing a chroman skeleton such as (-)-chromazonarol, (+)-8-epi-puupehedione, a key synthetic intermediate of (+)-wiedendiol, and (-)-11'-deoxytaondiol methyl ether.
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Ishibashi
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D002839:Chromans / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*; D014966:Xanthenes / Q000138:chemical synthesis
chemical_list: C499734:11'-deoxytaondiol methyl ether; C481243:8-epipuupehedione; D002839:Chromans; D004987:Ethers; D013729:Terpenes; D014966:Xanthenes; C121655:chromazonarol