Side–chain opening of steroidal sapogenins to form 22–oxocholestanic skeletons. An approach to analogues of the aglycone of the potent anticancer agent OSW–1
María A. Fernández–Herrera, Jesús Sandoval–Ramírez,* Socorro Meza–Reyes, and Sara Montiel–Smith
Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla. Ciudad Universitaria, San Manuel, 72570 Puebla, Pue., México.*Responsible author: jsandova@siu.buap.mx
Received June 5, 2009
Accepted August 31, 2009
Abstract
The side–chain opening of 25R and 25S steroidal sapogenins to form 22–oxocholestanic skeletons is described. The transformation was produced under mild conditions providing high yields (70–87%), in a one pot procedure (some acetylated starting material is recovered). This methodology yields 17–deoxy–26–oxy analogues of the aglycone of the potent anticancer agent OSW–1. All products were fully characterized by 1D and 2D NMR; the most representative displacements are briefly discussed.
Keywords: steroidal sapogenins, acetolysis, aglycone, OSW–1.
Resumen
Se reporta la apertura de la cadena lateral de sapogeninas esteroidales 25R y 25S para obtener estructuras 22–oxocolestánicas. La transformación fue llevada a cabo bajo condiciones de reacción suaves y con altos rendimientos (70–87%), en un solo paso (se recupera materia prima acetilada). Con esta metodología se obtienen, en un solo paso, análogos 17–desoxi–26–oxigenados de la aglicona del potente anticancerígeno OSW–1. Todos los productos fueron caracterizados por RMN de una y dos dimensiones y los desplazamientos más representativos se discuten brevemente.
Palabras clave: sapogeninas esteroidales, acetólisis, aglicona, OSW–1.
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]]>Acknowledgements
The authors gratefully thank CONACYT for the scholarship to MAFH, and to PROQUINA for diosgenin gift.
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