Synthesis of NH006 - A photostable fungicide effective against Botrytis cinerea - According to the asymmetric total synthesis of MK8383

Nobuyuki Hayashi, Kentaro Yamamoto, Nobuto Minowa, Masaaki Mitomi, Masahisa Nakada

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    MK8383, isolated from Phoma sp. T2526 in 1993, exhibits potent antibiotic activities against a variety of phytopathogens and has been considered a promising fungicide against Botrytis cinerea. Unfortunately, MK8383 is a photosensitive compound and it undergoes irreversible decomposition. Although much effort has been devoted to improving the photostability of MK8383 by chemical modification of its structure by a research group organized by Meiji Seika Kaishya, Ltd. and Mitsubishi Chemical Corporation, a photostable MK8383 derivative has never been prepared. We have found that a C13-14 double bond of MK8383 and (+)-phomopsidin is responsible for the photosensitivity, and herein, we report the synthesis of NH006, an MK8383 derivative with a saturated C13-14 double bond and (S) configuration at C14, based on the asymmetric total synthesis of MK8383. NH006 exhibits good photostability and potent antifungal activity against B. cinerea.

    Original languageEnglish
    Pages (from-to)1821-1825
    Number of pages5
    JournalOrganic and Biomolecular Chemistry
    Volume8
    Issue number8
    DOIs
    Publication statusPublished - 2010

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    fungicides
    Botrytis
    Fungicides
    Anti-Bacterial Agents
    Derivatives
    Photosensitivity
    antibiotics
    photosensitivity
    Chemical modification
    synthesis
    Research
    Decomposition
    decomposition
    configurations
    Industry
    phomopsidin

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Biochemistry

    Cite this

    Synthesis of NH006 - A photostable fungicide effective against Botrytis cinerea - According to the asymmetric total synthesis of MK8383. / Hayashi, Nobuyuki; Yamamoto, Kentaro; Minowa, Nobuto; Mitomi, Masaaki; Nakada, Masahisa.

    In: Organic and Biomolecular Chemistry, Vol. 8, No. 8, 2010, p. 1821-1825.

    Research output: Contribution to journalArticle

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