title: An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes.
abstract: Enantiomerically pure (1S,3S)- and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanes have been efficiently synthesized from L-aspartic acid. The title compounds are isosteres of ribose and may be used to construct nucleoside analogs with important antiviral and antineoplastic activities as demonstrated by a concise total synthesis of (+)-4'-deoxycarbapentostatin nucleoside.
authors.affiliation: Department of Chemistry, University of California, Berkeley 94720, USA.
authors.forename: Henry
authors.initials: H
authors.lastname: Rapoport
authors.forename: Yuewu
authors.initials: Y
authors.lastname: Chen
authors.forename: Rafat M
authors.initials: RM
authors.lastname: Mohareb
authors.forename: Jin Hee
authors.initials: JH
authors.lastname: Ahn
authors.forename: Tae Bo
authors.initials: TB
authors.lastname: Sim
authors.forename: Jonathan Z
authors.initials: JZ
authors.lastname: Ho
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D003517:Cyclopentanes