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

    19 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
    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.
    @article{f3f7c88f6ae94c59a2663ea9b46eb6f6,
    title = "The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor",
    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).",
    keywords = "Hauser annulation, Hibarimicin, Hibarimicinone, Thiolactone, Total synthesis",
    author = "Kuniaki Tatsuta and Tomohiro Fukuda and Tatsuya Ishimori and Rearu Yachi and Shinpei Yoshida and Hiroshi Hashimoto and Seijiro Hosokawa",
    year = "2012",
    month = "1",
    day = "25",
    doi = "10.1016/j.tetlet.2011.11.062",
    language = "English",
    volume = "53",
    pages = "422--425",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "4",

    }

    TY - JOUR

    T1 - The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

    AU - Tatsuta, Kuniaki

    AU - Fukuda, Tomohiro

    AU - Ishimori, Tatsuya

    AU - Yachi, Rearu

    AU - Yoshida, Shinpei

    AU - Hashimoto, Hiroshi

    AU - Hosokawa, Seijiro

    PY - 2012/1/25

    Y1 - 2012/1/25

    N2 - 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).

    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).

    KW - Hauser annulation

    KW - Hibarimicin

    KW - Hibarimicinone

    KW - Thiolactone

    KW - Total synthesis

    UR - http://www.scopus.com/inward/record.url?scp=84155167079&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84155167079&partnerID=8YFLogxK

    U2 - 10.1016/j.tetlet.2011.11.062

    DO - 10.1016/j.tetlet.2011.11.062

    M3 - Article

    VL - 53

    SP - 422

    EP - 425

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 4

    ER -