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Molecules 2016, 21(9), 1139; doi:10.3390/molecules21091139

Structural Modifications of Deoxycholic Acid to Obtain Three Known Brassinosteroid Analogues and Full NMR Spectroscopic Characterization

1
Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile
2
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 22 July 2016 / Revised: 24 August 2016 / Accepted: 25 August 2016 / Published: 27 August 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1384 KB, uploaded 27 August 2016]   |  

Abstract

An 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 516, which were previously reported only in partial form. View Full-Text
Keywords: synthesis; deoxycholic acid derivatives; brassinosteroid analogues; full NMR spectroscopic characterization synthesis; deoxycholic acid derivatives; brassinosteroid analogues; full NMR spectroscopic characterization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Herrera, H.; Carvajal, R.; Olea, A.F.; Espinoza, L. Structural Modifications of Deoxycholic Acid to Obtain Three Known Brassinosteroid Analogues and Full NMR Spectroscopic Characterization. Molecules 2016, 21, 1139.

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