The first total synthesis and structural determination of (+)-BE-52440A

Kuniaki Tatsuta, Yoshikazu Suzuki, Tatsuya Toriumi, Yoshiaki Furuya, Seijiro Hosokawa

    Research output: Contribution to journal › Article

    18 Citations (Scopus)

    Abstract

    The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including SN2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone.

    Original languageEnglish
    Pages (from-to)8018-8021
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number45
    DOIs
    Publication statusPublished - 2007 Nov 5

    Fingerprint

    Regioselectivity
    Dimerization
    Epoxy Compounds
    Dimers
    BE 52440 A
    sodium sulfide
    kalafungin

    Keywords

    • BE-52440A
    • Dimerization
    • Enantiodivergent synthesis
    • Tetrasubstituted epoxide
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    The first total synthesis and structural determination of (+)-BE-52440A. / Tatsuta, Kuniaki; Suzuki, Yoshikazu; Toriumi, Tatsuya; Furuya, Yoshiaki; Hosokawa, Seijiro.

    In: Tetrahedron Letters, Vol. 48, No. 45, 05.11.2007, p. 8018-8021.

    Research output: Contribution to journal › Article

    Tatsuta, K, Suzuki, Y, Toriumi, T, Furuya, Y & Hosokawa, S 2007, 'The first total synthesis and structural determination of (+)-BE-52440A', Tetrahedron Letters, vol. 48, no. 45, pp. 8018-8021. https://doi.org/10.1016/j.tetlet.2007.09.039
    Tatsuta K, Suzuki Y, Toriumi T, Furuya Y, Hosokawa S. The first total synthesis and structural determination of (+)-BE-52440A. Tetrahedron Letters. 2007 Nov 5;48(45):8018-8021. https://doi.org/10.1016/j.tetlet.2007.09.039
    Tatsuta, Kuniaki ; Suzuki, Yoshikazu ; Toriumi, Tatsuya ; Furuya, Yoshiaki ; Hosokawa, Seijiro. / The first total synthesis and structural determination of (+)-BE-52440A. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 45. pp. 8018-8021.
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    AU - Hosokawa, Seijiro

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