The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)

Kuniaki Tatsuta, Sonoko Tokishita, Tomohiro Fukuda, Takaaki Kano, Tadaaki Komiya, Seijiro Hosokawa

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    14 Citations (Scopus)

    Abstract

    K1115 B1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of 1H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B (the major isomer) and K1115 B (the minor isomer) were (1R, 17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B1, might be another mixture of stereoisomers.

    Original languageEnglish
    Pages (from-to)983-986
    Number of pages4
    JournalTetrahedron Letters
    Volume52
    Issue number9
    DOIs
    Publication statusPublished - 2011 Mar 2

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    Keywords

    • Alnumycin
    • BE-41956A
    • K1115 B
    • Michael-Dieckmann type condensation
    • Structural determination
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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