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

dc.contributor.authorOyarce J.
dc.contributor.authorAitken V.
dc.contributor.authorGonzález C.
dc.contributor.authorFerrer K.
dc.contributor.authorOlea A.F.
dc.contributor.authorParella T.
dc.contributor.authorCatalán L.E.
dc.date.accessioned2020-09-02T22:25:13Z
dc.date.available2020-09-02T22:25:13Z
dc.date.issued2019
dc.identifier10.3390/molecules24244612
dc.identifier.citation24, 24, -
dc.identifier.issn14203049
dc.identifier.urihttps://hdl.handle.net/20.500.12728/5699
dc.descriptionNatural 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.
dc.language.isoen
dc.publisherMDPI AG
dc.subject24-nor-5α-cholane
dc.subjectAnalogues
dc.subjectBrassinosteroid
dc.subjectSynthesis
dc.subjectbrassinosteroid
dc.subjectcholane derivative
dc.subjectphytohormone
dc.subjectchemical structure
dc.subjectchemistry
dc.subjecthydroxylation
dc.subjectnuclear magnetic resonance spectroscopy
dc.subjectsynthesis
dc.subjectBrassinosteroids
dc.subjectChemistry Techniques, Synthetic
dc.subjectCholanes
dc.subjectHydroxylation
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectMolecular Structure
dc.subjectPlant Growth Regulators
dc.titleSynthesis and structural determination of new brassinosteroid 24-nor-5α-cholane type analogs
dc.typeArticle


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