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

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

    Research output: Contribution to journal › Article

    13 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 1α (the major isomer) and K1115 B1β (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

    Fingerprint

    Stereoisomerism
    Optical rotation
    Anti-Bacterial Agents
    Optical Rotation
    Isomers
    Rhamnose
    Streptomyces
    Nuclear magnetic resonance
    Derivatives
    alnumycin

    Keywords

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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins). / Tatsuta, Kuniaki; Tokishita, Sonoko; Fukuda, Tomohiro; Kano, Takaaki; Komiya, Tadaaki; Hosokawa, Seijiro.

    In: Tetrahedron Letters, Vol. 52, No. 9, 02.03.2011, p. 983-986.

    Research output: Contribution to journal › Article

    Tatsuta, K, Tokishita, S, Fukuda, T, Kano, T, Komiya, T & Hosokawa, S 2011, 'The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)', Tetrahedron Letters, vol. 52, no. 9, pp. 983-986. https://doi.org/10.1016/j.tetlet.2010.12.061
    Tatsuta K, Tokishita S, Fukuda T, Kano T, Komiya T, Hosokawa S. The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins). Tetrahedron Letters. 2011 Mar 2;52(9):983-986. https://doi.org/10.1016/j.tetlet.2010.12.061
    Tatsuta, Kuniaki ; Tokishita, Sonoko ; Fukuda, Tomohiro ; Kano, Takaaki ; Komiya, Tadaaki ; Hosokawa, Seijiro. / The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins). In: Tetrahedron Letters. 2011 ; Vol. 52, No. 9. pp. 983-986.
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