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Rapid conversion of spirostans into furostan skeletons at room temperature |
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| Authors: | Viñas-Bravo Omar Martinez-Pascual Roxana Vega-Baez José Luis Gómez-Calvario Víctor Sandoval-Ramírez Jesús Montiel-Smith Sara Meza-Reyes Socorro López-De Rosas Alejandra Martínez-Montiel Mónica Reyes Mayra Ruiz José A |
| Affiliation: | Universidad del Papaloapan, Colonia Parque Industrial, Tuxtepec, Oax., México CP, Mexico. |
| Abstract: | We report a facile protocol to obtain 22-substituted furostans and pseudosapogenins in high yields from (25R)- and (25S)-sapogenins. This method involves the treatment of the sapogenin with acetic-trifluoroacetic mixed anhydride and BF(3)·OEt(2) at room temperature, followed by the addition of a nucleophile (H(2)O, MeOH or KSeCN). In the case of 22-hydroxyfurostans, they can be transformed to pseudosapogenins by treatment with p-toluensulfonic acid. |
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