A facile synthesis of (+)/(−)-pentenomycin I and analogs, and their antimicrobial evaluation

Takaaki Kamishima, Masato Suzuki, Shigenobu Aoyagi, Toshihiro Watanabe, Yoshitaka Koseki, Hitoshi Kasai

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)


    This study reported a stereoselective synthesis of (+)/(+)-pentenomycin I in 4–5 steps through regioselective silylation, optical resolution and dihydroxylation, followed by an olefin formation, from a known racemic cyclopentenone prepared from 2-deoxy-D-glucose. We also accomplished the transformation of a common intermediate into a variety of analogs. In addition, the antimicrobial activities of the pentenomycin analogs were evaluated, which revealed important structural factors of pentenomycins for the antimicrobial activities.

    Original languageEnglish
    Pages (from-to)1375-1378
    Number of pages4
    JournalTetrahedron Letters
    Issue number20
    Publication statusPublished - 2019 May 16


    • Antimicrobial susceptibility testing
    • Pentenomycin
    • Structure-activity relationships
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry


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