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

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    1 Citation (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)1190-1195
    Number of pages6
    JournalChemical and Pharmaceutical Bulletin
    Volume64
    Issue number8
    DOIs
    Publication statusPublished - 2016

    Keywords

    • 19-Norvitamin D
    • cis-A ring synthon
    • Julia-Kocienski coupling

    ASJC Scopus subject areas

    • Chemistry(all)
    • Drug Discovery

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  • Cite this

    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, 64(8), 1190-1195. https://doi.org/10.1248/cpb.c16-00311