Reinvestigation of the stereochemistry of kulokekahilide-2

Yuuki Takada, Eriko Mori, Masahiro Umehara, Youichi Nakao, Junji Kimura

    Research output: Contribution to journalArticle

    13 Citations (Scopus)

    Abstract

    An attempt to carry out a total synthesis of kulokekahilide-2 (1) by macrolactonization of a seco acid prepared from a suitably protected hexapeptide and a dioxy acid moiety unexpectedly resulted in the formation of the 43-epimer (1a) of the cytotoxic depsipeptide, for which structure 1b has previously been proposed. A second attempt involving macrolactamization of the corresponding amino acid gave the target product, 1b, but the spectral data of the product did not match those of natural 1. Furthermore, neither 1a nor 1b showed any cytotoxicity, from which it is concluded that the structure of natural 1 is incorrect and should be re-examined.

    Original languageEnglish
    Pages (from-to)7653-7656
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number43
    DOIs
    Publication statusPublished - 2007 Oct 22

    Fingerprint

    Stereochemistry
    Depsipeptides
    Acids
    Cytotoxicity
    Amino Acids
    kulokekahilide-2
    kulokekahilide-1

    Keywords

    • 43-epi-Kulokekahilide-2
    • Cytotoxicity
    • Kulokekahilide-2

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Reinvestigation of the stereochemistry of kulokekahilide-2. / Takada, Yuuki; Mori, Eriko; Umehara, Masahiro; Nakao, Youichi; Kimura, Junji.

    In: Tetrahedron Letters, Vol. 48, No. 43, 22.10.2007, p. 7653-7656.

    Research output: Contribution to journalArticle

    Takada, Yuuki ; Mori, Eriko ; Umehara, Masahiro ; Nakao, Youichi ; Kimura, Junji. / Reinvestigation of the stereochemistry of kulokekahilide-2. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 43. pp. 7653-7656.
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