Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3

Kosuke Usuda, Tanima Biswas, Takuya Yamaguchi, Yusuke Akagi, Koji Yasui, Motonari Uesugi, Isao Shimizu, Seijiro Hosokawa, Kazuo Nagasawa

    研究成果: Article

    抄録

    1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.

    元の言語English
    ページ(範囲)1190-1195
    ページ数6
    ジャーナルChemical and Pharmaceutical Bulletin
    64
    発行部数8
    DOI
    出版物ステータスPublished - 2016

    Fingerprint

    Quinic Acid
    Benzoates
    Nuclear magnetic resonance
    Circular Dichroism
    Experiments
    1,25-dihydroxy-19-norvitamin D3

    ASJC Scopus subject areas

    • Chemistry(all)
    • Drug Discovery

    これを引用

    Usuda, K., Biswas, T., Yamaguchi, T., Akagi, Y., Yasui, K., Uesugi, M., ... Nagasawa, K. (2016). Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3 Chemical and Pharmaceutical Bulletin, 64(8), 1190-1195. https://doi.org/10.1248/cpb.c16-00311

    Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3 . / Usuda, Kosuke; Biswas, Tanima; Yamaguchi, Takuya; Akagi, Yusuke; Yasui, Koji; Uesugi, Motonari; Shimizu, Isao; Hosokawa, Seijiro; Nagasawa, Kazuo.

    :: Chemical and Pharmaceutical Bulletin, 巻 64, 番号 8, 2016, p. 1190-1195.

    研究成果: Article

    Usuda, K, Biswas, T, Yamaguchi, T, Akagi, Y, Yasui, K, Uesugi, M, Shimizu, I, Hosokawa, S & Nagasawa, K 2016, 'Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3 ', Chemical and Pharmaceutical Bulletin, 巻. 64, 番号 8, pp. 1190-1195. https://doi.org/10.1248/cpb.c16-00311
    Usuda K, Biswas T, Yamaguchi T, Akagi Y, Yasui K, Uesugi M その他. Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3 Chemical and Pharmaceutical Bulletin. 2016;64(8):1190-1195. https://doi.org/10.1248/cpb.c16-00311
    Usuda, Kosuke ; Biswas, Tanima ; Yamaguchi, Takuya ; Akagi, Yusuke ; Yasui, Koji ; Uesugi, Motonari ; Shimizu, Isao ; Hosokawa, Seijiro ; Nagasawa, Kazuo. / Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3 :: Chemical and Pharmaceutical Bulletin. 2016 ; 巻 64, 番号 8. pp. 1190-1195.
    @article{c24dcb280ba447cf90ae2bb41f763cd7,
    title = "Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3",
    abstract = "1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.",
    keywords = "19-Norvitamin D, cis-A ring synthon, Julia-Kocienski coupling",
    author = "Kosuke Usuda and Tanima Biswas and Takuya Yamaguchi and Yusuke Akagi and Koji Yasui and Motonari Uesugi and Isao Shimizu and Seijiro Hosokawa and Kazuo Nagasawa",
    year = "2016",
    doi = "10.1248/cpb.c16-00311",
    language = "English",
    volume = "64",
    pages = "1190--1195",
    journal = "Chemical and Pharmaceutical Bulletin",
    issn = "0009-2363",
    publisher = "Pharmaceutical Society of Japan",
    number = "8",

    }

    TY - JOUR

    T1 - Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3

    AU - Usuda, Kosuke

    AU - Biswas, Tanima

    AU - Yamaguchi, Takuya

    AU - Akagi, Yusuke

    AU - Yasui, Koji

    AU - Uesugi, Motonari

    AU - Shimizu, Isao

    AU - Hosokawa, Seijiro

    AU - Nagasawa, Kazuo

    PY - 2016

    Y1 - 2016

    N2 - 1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.

    AB - 1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.

    KW - 19-Norvitamin D

    KW - cis-A ring synthon

    KW - Julia-Kocienski coupling

    UR - http://www.scopus.com/inward/record.url?scp=84982746757&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84982746757&partnerID=8YFLogxK

    U2 - 10.1248/cpb.c16-00311

    DO - 10.1248/cpb.c16-00311

    M3 - Article

    VL - 64

    SP - 1190

    EP - 1195

    JO - Chemical and Pharmaceutical Bulletin

    JF - Chemical and Pharmaceutical Bulletin

    SN - 0009-2363

    IS - 8

    ER -