title: Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin.
abstract: The first total synthesis and structure revision of (-)-11β-hydroxycurvularin (1b), a macrolide possessing a β-hydroxyketone moiety, were accomplished. The β-hydroxyketone moiety in this natural product was introduced by cleavage of the N-O bond in an isoxazoline ring that was formed diastereoselectively in a 1,5-remote stereocontrolled fashion by employing intramolecular nitrile oxide cycloaddition.
authors.affiliation: Drug Discovery Division, Korea Research Institute of Chemical Technology , Yuseong, Daejeon 34114, Republic of Korea.
authors.forename: Hyeonjeong
authors.initials: H
authors.lastname: Choe
authors.affiliation: College of Pharmacy, Kangwon National University , 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 24341, Republic of Korea.
authors.forename: Thuy Trang
authors.initials: TT
authors.lastname: Pham
authors.affiliation: Drug Discovery Division, Korea Research Institute of Chemical Technology , Yuseong, Daejeon 34114, Republic of Korea.
authors.forename: Joo Yun
authors.initials: JY
authors.lastname: Lee
authors.affiliation: Drug Discovery Division, Korea Research Institute of Chemical Technology , Yuseong, Daejeon 34114, Republic of Korea.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Latif
authors.affiliation: College of Pharmacy, Kangwon National University , 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 24341, Republic of Korea.
authors.forename: Haeil
authors.initials: H
authors.lastname: Park
authors.affiliation: Department of Chemistry, Chungbuk National University , 1 Chungdae-ro, Seowon-gu, Cheongju, Chungbuk 28644, Republic of Korea.
authors.forename: Young Kee
authors.initials: YK
authors.lastname: Kang
authors.affiliation: College of Pharmacy, Kangwon National University , 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 24341, Republic of Korea.
authors.forename: Jongkook
authors.initials: J
authors.lastname: Lee
mesh_terms: D001688:Biological Products; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000737:chemistry; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D015025:Zearalenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C000610871:11beta-hydroxycurvularin; D001688:Biological Products; D007555:Isoxazoles; D009570:Nitriles; D009569:Nitric Oxide; D015025:Zearalenone