1380412-87-2Relevant academic research and scientific papers
An unexpected BF3·Et2O-catalyzed rearrangement of 23E-benzylidenespirostanes to spiro[furan-indenes]
Ramos Enríquez, Manuel A.,Flores-álamo, Marcos,Iglesias-Arteaga, Martín A.
, p. 2249 - 2252 (2016)
Treatment of 23E-benzylidenespirostanes with BF3·Et2O in 2/1 acetic acid/CH2Cl2 led to novel steroids bearing a spiro[furan-indene] moiety in the side chain. When steroid sapogenins were treated with benzaldehyde and BF3·Et2O in the same mixture of solvents, similar compounds were obtained. The structures of the novel spirocyclic steroids were confirmed by NMR and X-ray diffraction.
BF3·Et2O-induced stereoselective aldol reaction with benzaldehyde, and steroid sapogenins and its application to a convenient synthesis of dinorcholanic lactones
Ruíz-Pérez, Karen M.,Romero-ávila, Margarita,Tinajero-Delgado, Verónica,Flores-álamo, Marcos,Iglesias-Arteaga, Martín A.
experimental part, p. 819 - 828 (2012/07/03)
Treatment of steroid sapogenins with benzaldehyde and BF 3·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.
