title: Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides.
abstract: The preparative and stereoselective synthesis (45- 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.
authors.affiliation: WonJun Choi Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Young Mi
authors.initials: YM
authors.lastname: Ko
authors.forename: Hye Jin
authors.initials: HJ
authors.lastname: Kim
authors.forename: Jeong A
authors.initials: JA
authors.lastname: Lee
authors.forename: Kang Man
authors.initials: KM
authors.lastname: Lee
authors.forename: Mi Kyung
authors.initials: MK
authors.lastname: Yun
authors.forename: Dae Hong
authors.initials: DH
authors.lastname: Shin
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
authors.forename: Yhun Y
authors.initials: YY
authors.lastname: Sheen
authors.forename: Kilhyoun
authors.initials: K
authors.lastname: Kim
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D009705:Nucleosides / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C506206:3-hydroxymethylcyclopentenone; D000438:Alcohols; D003517:Cyclopentanes; D009705:Nucleosides; D012266:Ribose; C013905:cyclopentenone; D010100:Oxygen