Concise synthesis of the C15-C38 fragment of okadaic acid, a specific inhibitor of protein phosphatases 1 and 2A

Haruhiko Fuwa, Keita Sakamoto, Takashi Muto, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    Abstract A marine polyether natural product okadaic acid is known to be a potent and specific inhibitor of protein phosphatases 1 and 2A. Herein, concise synthesis of the C15-C38 fragment of okadaic acid is reported. We investigated two different strategies for the construction of two spiroacetal substructures found in the target compound. The first strategy involved Suzuki-Miyaura coupling for the synthesis of endocyclic enol ethers and subsequent spiroacetalization. The second strategy exploited Suzuki-Miyaura coupling for the synthesis of exo-olefins as the precursor of spiroacetals. An alkynylaluminum-anomeric sulfone coupling effectively assembled the key spiroacetal substructures and completed the target compound.

    Original languageEnglish
    Article number26603
    Pages (from-to)6369-6383
    Number of pages15
    JournalTetrahedron
    Volume71
    Issue number37
    DOIs
    Publication statusPublished - 2015 Aug 7

    Keywords

    • Anomeric sulfones
    • Marine toxins
    • Polyethers
    • Spiroacetals
    • Suzuki-Miyaura coupling

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'Concise synthesis of the C15-C38 fragment of okadaic acid, a specific inhibitor of protein phosphatases 1 and 2A'. Together they form a unique fingerprint.

    Cite this