A new artificial cyclase for polyprenoids: enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11'-deoxytaondiol methyl ether.
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.
Ishibashi
Hideaki
H
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Ishihara
Kazuaki
K
Yamamoto
Hisashi
H
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
C499734:11'-deoxytaondiol methyl ether; C481243:8-epipuupehedione; D002839:Chromans; D004987:Ethers; D013729:Terpenes; D014966:Xanthenes; C121655:chromazonarol