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    Synthesis and structural determination of new brassinosteroid 24-nor-5α-cholane type analogs

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    item_2-s2.0-85076631892.pdf (2.759Kb)
    Date
    2019
    DOI
    10.3390/molecules24244612

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    Author
    Oyarce J.
    Aitken V.
    González C.
    Ferrer K.
    Olea A.F.
    Parella T.
    Catalán L.E.
    Abstract
    Natural brassinosteroids possess a 22R, 23R configuration that appears essential for biological activity. It is, therefore, interesting to elucidate if the activity of brassinosteroids with a short side chain depends on the C22 configuration. Herein, we describe the synthesis of new brassinosteroids analogs with 24-norcholane type of side chain and R configuration at C22. The initial reaction is the dihydroxylation of a terminal olefin that leads to S/R epimers. Three different methods were tested in order to evaluate the obtained S/R ratio and the reaction yields. The results indicate that Upjohn dihydroxylation is the most selective reaction giving a 1.0:0.24 S/R ratio, whereas a Sharpless reaction leads to a mixture of 1.0:0.90 S/R with 95% yield. Using the latter mixture and following a previous reported method, benzoylated derivatives and both S and R brassinosteroids analogs were synthesized. All synthesized compounds were completely characterized by NMR spectroscopy, and HRMS of new compounds are also given. In conclusion, a synthetic route for preparation of new analogs of brassinosteroids of 24-norcholane type and R configuration at C22 were described. It is expected that this will help to elucidate if a configuration at C22 is a structural requirement for hormonal growth activity in plants. © 2019 by the authors.
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    LA UNIVERSIDAD
    • Aseguramiento de Calidad
    • Internacional
    • Vinculación con el Medio
    • Más Transparencia
    • Acreditación
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    FACULTADES
    • Administración y Negocios
    • Arquitectura y Construcción
    • Ciencias de la Salud
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    • Ingeniería
    INVESTIGACIÓN
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