The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Kuniaki Tatsuta, Tomohiro Fukuda, Tatsuya Ishimori, Rearu Yachi, Shinpei Yoshida, Hiroshi Hashimoto, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    18 Citations (Scopus)

    Abstract

    The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag + gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).

    Original languageEnglish
    Pages (from-to)422-425
    Number of pages4
    JournalTetrahedron Letters
    Volume53
    Issue number4
    DOIs
    Publication statusPublished - 2012 Jan 25

    Fingerprint

    src-Family Kinases
    Aromatization
    Arabinose
    Skeleton
    Condensation
    Oxidation
    hibarimicinone

    Keywords

    • Hauser annulation
    • Hibarimicin
    • Hibarimicinone
    • Thiolactone
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor. / Tatsuta, Kuniaki; Fukuda, Tomohiro; Ishimori, Tatsuya; Yachi, Rearu; Yoshida, Shinpei; Hashimoto, Hiroshi; Hosokawa, Seijiro.

    In: Tetrahedron Letters, Vol. 53, No. 4, 25.01.2012, p. 422-425.

    Research output: Contribution to journalArticle

    Tatsuta, K, Fukuda, T, Ishimori, T, Yachi, R, Yoshida, S, Hashimoto, H & Hosokawa, S 2012, 'The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor', Tetrahedron Letters, vol. 53, no. 4, pp. 422-425. https://doi.org/10.1016/j.tetlet.2011.11.062
    Tatsuta K, Fukuda T, Ishimori T, Yachi R, Yoshida S, Hashimoto H et al. The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor. Tetrahedron Letters. 2012 Jan 25;53(4):422-425. https://doi.org/10.1016/j.tetlet.2011.11.062
    Tatsuta, Kuniaki ; Fukuda, Tomohiro ; Ishimori, Tatsuya ; Yachi, Rearu ; Yoshida, Shinpei ; Hashimoto, Hiroshi ; Hosokawa, Seijiro. / The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 4. pp. 422-425.
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