title: Biomimetic asymmetric total synthesis of (-)-laurefucin via an organoselenium-mediated intramolecular hydroxyetherification.
abstract: The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.
authors.affiliation: The Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Byungsook
authors.initials: B
authors.lastname: Kim
authors.forename: Miseon
authors.initials: M
authors.lastname: Lee
authors.forename: Mi Jung
authors.initials: MJ
authors.lastname: Kim
authors.forename: Hyunjoo
authors.initials: H
authors.lastname: Lee
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
authors.forename: Minseob
authors.initials: M
authors.lastname: Koh
authors.forename: Seung Bum
authors.initials: SB
authors.lastname: Park
authors.forename: Kye Jung
authors.initials: KJ
authors.lastname: Shin
mesh_terms: D032701:Biomimetics; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004987:Ethers; D005663:Furans; D016566:Organoselenium Compounds; C017459:laurefucin