Total Syntheses of Stoloniferol B and Penicitol A, and Structural Revision of Fusaraisochromanone

Tatsuki Ohashi, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.

    Original languageEnglish
    Pages (from-to)3021-3024
    Number of pages4
    JournalOrganic Letters
    Volume20
    Issue number10
    DOIs
    Publication statusPublished - 2018 May 18

    Fingerprint

    Citrinin
    Enantiomers
    Esterification
    enantiomers
    Cyclization
    Hot Temperature
    Michael reaction
    Derivatives
    synthesis
    methyl acetoacetate
    3-hydroxybutanal
    penicitol A

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Total Syntheses of Stoloniferol B and Penicitol A, and Structural Revision of Fusaraisochromanone. / Ohashi, Tatsuki; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 20, No. 10, 18.05.2018, p. 3021-3024.

    Research output: Contribution to journalArticle

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    author = "Tatsuki Ohashi and Seijiro Hosokawa",
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    AB - The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.

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