An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes

Henry Rapoport, Yuewu Chen, Rafat M. Mohareb, Jin Hee Ahn, Tae Bo Sim, Jonathan Z. Ho

    Research output: Contribution to journalArticlepeer-review

    4 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)1153-1156
    Number of pages4
    JournalChemical and Pharmaceutical Bulletin
    Volume51
    Issue number10
    DOIs
    Publication statusPublished - 2003 Oct

    Keywords

    • Amino acid
    • Carbocycle
    • Enantioselectivity
    • Heterocycle
    • Nucleoside

    ASJC Scopus subject areas

    • General Chemistry
    • Drug Discovery

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