One-Step conversion to a disubstituted cyclopentenone from 2-Deoxy-D-Glucose and application to synthesis of prostaglandin e1 methyl ester

Takaaki Kamishima, Toshiyuki Nonaka, Toshihiro Watanabe, Yoshitaka Koseki, Hitoshi Kasai

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    We have developed a facile one-step conversion of 2-deoxy-D-glucose to form a disubstituted cyclopentenone through catalyst-free hydrothermal reaction under mild conditions. The use of 2-deoxy-D-glucose in one-pot conversion is to provide the formation of a carbon five-membered ring instead of the common biomass-derived furans such as furfural, 5-HMF, etc. The cyclopentenone has a potential to be a building block for the preparation of chemical products. As one example, we successfully demonstrated the synthesis of prostaglandin E1 methyl ester.

    Original languageEnglish
    Pages (from-to)1691-1696
    Number of pages6
    JournalBulletin of the Chemical Society of Japan
    Volume91
    Issue number12
    DOIs
    Publication statusPublished - 2018 Jan 1

    Keywords

    • Biomass
    • Hydrothermal reaction
    • Total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)

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