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Synthesis and structural determination of new brassinosteroid 24-nor-5α-cholane type analogs
dc.contributor.author | Oyarce J. | |
dc.contributor.author | Aitken V. | |
dc.contributor.author | González C. | |
dc.contributor.author | Ferrer K. | |
dc.contributor.author | Olea A.F. | |
dc.contributor.author | Parella T. | |
dc.contributor.author | Catalán L.E. | |
dc.date.accessioned | 2020-09-02T22:25:13Z | |
dc.date.available | 2020-09-02T22:25:13Z | |
dc.date.issued | 2019 | |
dc.identifier | 10.3390/molecules24244612 | |
dc.identifier.citation | 24, 24, - | |
dc.identifier.issn | 14203049 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12728/5699 | |
dc.description | 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. | |
dc.language.iso | en | |
dc.publisher | MDPI AG | |
dc.subject | 24-nor-5α-cholane | |
dc.subject | Analogues | |
dc.subject | Brassinosteroid | |
dc.subject | Synthesis | |
dc.subject | brassinosteroid | |
dc.subject | cholane derivative | |
dc.subject | phytohormone | |
dc.subject | chemical structure | |
dc.subject | chemistry | |
dc.subject | hydroxylation | |
dc.subject | nuclear magnetic resonance spectroscopy | |
dc.subject | synthesis | |
dc.subject | Brassinosteroids | |
dc.subject | Chemistry Techniques, Synthetic | |
dc.subject | Cholanes | |
dc.subject | Hydroxylation | |
dc.subject | Magnetic Resonance Spectroscopy | |
dc.subject | Molecular Structure | |
dc.subject | Plant Growth Regulators | |
dc.title | Synthesis and structural determination of new brassinosteroid 24-nor-5α-cholane type analogs | |
dc.type | Article |