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Structural modifications of deoxycholic acid to obtain three known brassinosteroid analogues and full NMR spectroscopic characterization

dc.contributor.authorHerrera H.
dc.contributor.authorCarvajal R.
dc.contributor.authorOlea A.F.
dc.contributor.authorEspinoza L.
dc.date.accessioned2020-09-02T22:20:38Z
dc.date.available2020-09-02T22:20:38Z
dc.date.issued2016
dc.identifier10.3390/molecules21091139
dc.identifier.citation21, 9, -
dc.identifier.issn14203049
dc.identifier.urihttps://hdl.handle.net/20.500.12728/4948
dc.descriptionAn improved synthesis route for obtaining known brassinosteroid analogues, i.e., methyl 2α,3α-dihydroxy-6-oxo-5α-cholan-24-oate (11), methyl 3α-hydroxy-6-oxo-7-oxa-5α-cholan-24-oate (15) and methyl 3α-hydroxy-6-oxa-7-oxo-5α-cholan-24-oate (16), from hyodeoxycholic acid (4) maintaining the native side chain is described. In the alternative procedure, the di-oxidized product 6, obtained in the oxidation of methyl hyodeoxycholate 5, was converted almost quantitatively into the target monoketone 7 by stereoselective reduction with NaBH4 , increasing the overall yield of this synthetic route to 96.8%. The complete 1H- and 13C-NMR assignments for all compounds synthesized in this work have been made by 1D and 2D heteronuclear correlation gs-HSQC and gs-HMBC techniques. Thus, it was possible to update the spectroscopic information of 1H-NMR and to accomplish a complete assignment of all 13C-NMR signals for analogues 5-16, which were previously reported only in partial form. © 2016 by the authors;.
dc.language.isoen
dc.publisherMDPI AG
dc.subjectBrassinosteroid analogues
dc.subjectDeoxycholic acid derivatives
dc.subjectFull nmr spectroscopic
dc.subjectSynthesis
dc.subjectdeoxycholic acid
dc.subjectphytosterol
dc.subjectanalogs and derivatives
dc.subjectchemistry
dc.subjectnuclear magnetic resonance spectroscopy
dc.subjectsynthesis
dc.subjectDeoxycholic Acid
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectPhytosterols
dc.titleStructural modifications of deoxycholic acid to obtain three known brassinosteroid analogues and full NMR spectroscopic characterization
dc.typeArticle


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