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

    研究成果: Article

    20 引用 (Scopus)

    抄録

    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).

    元の言語English
    ページ（範囲）422-425
    ページ数4
    ジャーナルTetrahedron Letters
    巻53
    発行部数4
    DOI
    出版物ステータスPublished - 2012 1 25

    Fingerprint

    src-Family Kinases
    Aromatization
    Arabinose
    Skeleton
    Condensation
    Oxidation
    hibarimicinone

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    これを引用

    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.

    ：: Tetrahedron Letters, 巻 53, 番号 4, 25.01.2012, p. 422-425.

    研究成果: Article

    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, 巻. 53, 番号 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 その他. The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor. Tetrahedron Letters. 2012 1 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. ：: Tetrahedron Letters. 2012 ; 巻 53, 番号 4. pp. 422-425.
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    AU - Tatsuta, Kuniaki

    AU - Fukuda, Tomohiro

    AU - Ishimori, Tatsuya

    AU - Yachi, Rearu

    AU - Yoshida, Shinpei

    AU - Hashimoto, Hiroshi

    AU - Hosokawa, Seijiro

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    AB - 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).

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    KW - Total synthesis

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