title: Construction of eight-membered ether rings by olefin geometry-dependent internal alkylation: first asymmetric total syntheses of (+)-3-(E)- and (+)-3-(Z)-pinnatifidenyne.
abstract: The first and highly stereoselective asymmetric total syntheses of eight-membered ring ether marine natural products (+)-3-(E)-pinnatifidenyne and (+)-3-(Z)-pinnatifidenyne have been accomplished. Notable features of our syntheses include a novel and efficient construction of oxocene 5 by a highly stereo- and regioselective internal alkylation and direct ketone synthesis of ketone 16 from the alpha-alkyloxy amide moiety in oxocene 5.
authors.affiliation: Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, San 56-1, Shinrim-Dong, Kwanak-Ku, Seoul 151-742, Korea.
authors.forename: Hyoungsu
authors.initials: H
authors.lastname: Kim
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Jaeyoon
authors.initials: J
authors.lastname: Jung
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000478:Alkylation; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C480362:3-pinnatifidenyne; D004988:Ethers, Cyclic