title: Total synthesis of (-)-cinatrin C1 based on an In(OTf)3-catalyzed Conia-Ene reaction.
abstract: The stereocontrolled total synthesis of (-)-cinatrin C1, a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)3-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
authors.forename: Fumiya
authors.initials: F
authors.lastname: Urabe
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Nagashima
authors.forename: Keisuke
authors.initials: K
authors.lastname: Takahashi
authors.forename: Jun
authors.initials: J
authors.lastname: Ishihara
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
mesh_terms: D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D008698:Mesylates; C073569:cinatrin C1; C012077:trifluoromethanesulfonic acid