Rapid conversion of spirostans into furostan skeletons at room temperature
Omar Viñas-Bravo1, Roxana Martinez-Pascual, José Luis Vega-Baez
1Universidad 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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