Abstract

Treatment of steroid sapogenins with benzaldehyde and BF3·Et2O cleanly produces E-23(23′)-benzylidenspirostanes in good yields in a reaction pathway which consists on an aldol reaction followed by a dehydration step. The obtained E-23(23′)-benzylidenspirostanes can be easily converted to dinorcholanic lactones by treatment with CrO3 in acetic acid. The synthetic sequence to dinorcholanic lactones is compatible with the presence of double bonds and carbonyl groups in the steroid framework.

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