title: Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid.
abstract: Diastereoselective total synthesis of isocarbacyclin, which features a fused bicyclic key intermediate available from l-ascorbic acid, is described. The key intermediate was prepared in multigram quantities by the Pauson-Khand reaction of l-ascorbic acid-based (R)-4,4-diallyl-2,2-dimethyl-5-(trimethylsilyl)ethynyl-1,3-dioxolane (3), discriminating diastereotopic groups and faces of the geminal allyl substituents.
authors.affiliation: School of Education, and Department of Bioscience and Biotechnology, School of Engineering, Okayama University, Tsushima, Okayama, Japan.
authors.forename: Teruhiko
authors.initials: T
authors.lastname: Ishikawa
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Ishii
authors.forename: Kazuo
authors.initials: K
authors.lastname: Shimizu
authors.forename: Hiroe
authors.initials: H
authors.lastname: Nakao
authors.forename: Jin
authors.initials: J
authors.lastname: Urano
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kudo
authors.forename: Seiki
authors.initials: S
authors.lastname: Saito
mesh_terms: D001205:Ascorbic Acid / Q000737:chemistry*; D002384:Catalysis; D011464:Epoprostenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C041946:9-O-methanoprostaglandin I; D011464:Epoprostenol; D001205:Ascorbic Acid