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Synthesis of 2-deoxybrassinosteroids analogs with 24-nor, 22(s)-23-dihydroxy-type side chains from hyodeoxycholic acid

dc.contributor.authorCarvajal R.
dc.contributor.authorGonzález C.
dc.contributor.authorOlea A.F.
dc.contributor.authorFuentealba M.
dc.contributor.authorEspinoza L.
dc.date.accessioned2020-09-02T22:14:17Z
dc.date.available2020-09-02T22:14:17Z
dc.date.issued2018
dc.identifier10.3390/molecules23061306
dc.identifier.citation23, 6, -
dc.identifier.issn14203049
dc.identifier.urihttps://hdl.handle.net/20.500.12728/3942
dc.descriptionNatural brassinosteroids are widespread in the plant kingdom and it is known that they play an important role in regulating plant growth. In this study, two new brassinosteroid analogs with shorter side chains but keeping the diol function were synthesized. Thus, the synthesis of 2-deoxybrassinosteroids analogs of the 3α-hydroxy-24-nor, 22,23-dihydroxy-5α-cholestane side chain type is described. The starting material is a derivative from hyodeoxycholic acid (4), which was obtained with an overall yield of 59% following a previously reported five step route. The side chain of this intermediate was modified by oxidative decarboxylation to get a terminal olefin at the C22-C23 position (compound 20) and subsequent dihydroxylation of the olefin. The resulting epimeric mixture of 21a, 21b was separated and the absolute configuration at the C22 carbon for the main product 21a was elucidated by single crystal X-ray diffraction analysis of the benzoylated derivative 22. Finally, lactonization of 21a through a Baeyer-Villiger oxidation of triacetylated derivative 23, using CF3CO3H/CHCl3 as oxidant system, leads to lactones 24 and 25 in 35% and 14% yields, respectively. Deacetylation of these compounds leads to 2-deoxybrassinosteroids 18 and 19 in 86% and 81% yields. Full structural characterization of all synthesized compounds was achieved using their 1D, 2D NMR, and HRMS data. © 2018 by the authors.
dc.language.isoen
dc.publisherMDPI AG
dc.subject2-deoxybrassinosteroids
dc.subjectBrassinosteroid analogs
dc.subjectHyodeoxycholic acid
dc.subjectShort side chain
dc.subjectSynthesis
dc.subjectbrassinosteroid
dc.subjectdeoxycholic acid
dc.subjecthyodeoxycholic acid
dc.subjectlactone
dc.subjectdecarboxylation
dc.subjecthydroxylation
dc.subjectnuclear magnetic resonance spectroscopy
dc.subjectoxidation reduction reaction
dc.subjectstereoisomerism
dc.subjectsynthesis
dc.subjectX ray crystallography
dc.subjectBrassinosteroids
dc.subjectChemistry Techniques, Synthetic
dc.subjectCrystallography, X-Ray
dc.subjectDecarboxylation
dc.subjectDeoxycholic Acid
dc.subjectHydroxylation
dc.subjectLactones
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectOxidation-Reduction
dc.subjectStereoisomerism
dc.titleSynthesis of 2-deoxybrassinosteroids analogs with 24-nor, 22(s)-23-dihydroxy-type side chains from hyodeoxycholic acid
dc.typeArticle


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