Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A

Seijiro Hosokawa, Kazuya Yokota, Keisuke Imamura, Yasuaki Suzuki, Masataka Kawarasaki, Kuniaki Tatsuta

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    Abstract

    Actinopyrone A, an anti-Helicobacter pylori agent, was synthesized in nine steps from a silyl dienol ether. A vinylogous anti-aldol was stereoselectively synthesized by our developed remote stereoinduction methodology; coupling of this with a sulfone and a phosphonate species led to the construction of a vinylpyrone compound. This was submitted to reductive de-conjugation to give actinopyrone A. The absolute stereochemistry of actinopyrone A was determined to have the configuration 14R,15R.

    Original languageEnglish
    Pages (from-to)1415-1421
    Number of pages7
    JournalChemistry - An Asian Journal
    Volume3
    Issue number8-9
    DOIs
    Publication statusPublished - 2008 Sep 1

    Fingerprint

    Helicobacter pylori
    Organophosphonates
    Sulfones
    Stereochemistry
    Ether
    actinopyrone A
    3-hydroxybutanal

    Keywords

    • Actinopyrone A
    • Aldol reaction
    • Remote stereoinduction
    • Structural determination
    • Total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Hosokawa, S., Yokota, K., Imamura, K., Suzuki, Y., Kawarasaki, M., & Tatsuta, K. (2008). Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A. Chemistry - An Asian Journal, 3(8-9), 1415-1421. https://doi.org/10.1002/asia.200800109

    Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A. / Hosokawa, Seijiro; Yokota, Kazuya; Imamura, Keisuke; Suzuki, Yasuaki; Kawarasaki, Masataka; Tatsuta, Kuniaki.

    In: Chemistry - An Asian Journal, Vol. 3, No. 8-9, 01.09.2008, p. 1415-1421.

    Research output: Contribution to journalArticle

    Hosokawa, S, Yokota, K, Imamura, K, Suzuki, Y, Kawarasaki, M & Tatsuta, K 2008, 'Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A', Chemistry - An Asian Journal, vol. 3, no. 8-9, pp. 1415-1421. https://doi.org/10.1002/asia.200800109
    Hosokawa, Seijiro ; Yokota, Kazuya ; Imamura, Keisuke ; Suzuki, Yasuaki ; Kawarasaki, Masataka ; Tatsuta, Kuniaki. / Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A. In: Chemistry - An Asian Journal. 2008 ; Vol. 3, No. 8-9. pp. 1415-1421.
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