title: Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity.
abstract: The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.
authors.affiliation: 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: Byul Nae
authors.initials: BN
authors.lastname: Yoo
authors.forename: Jeong A
authors.initials: JA
authors.lastname: Lee
authors.forename: Dae Hong
authors.initials: DH
authors.lastname: Shin
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D015394:Molecular Structure; D009705:Nucleosides / Q000032:analysis / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012266:Ribose / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D009705:Nucleosides; D012266:Ribose; C031096:neplanocin A; D000241:Adenosine