The Conversion of Tomadine, a Steroidal Alkaloid, Into a Sapogenin

Two independent observations lead to the attempted conversion of tomatidine into sapogenin. E.H. White of Yale University has reported on the thermal deamination of aliphatic amines (1). This method had been adapted to the steroidal alkaloids by Sato and Latham (2), in which the reduction leads to the opening of the F ring and the formation of an H-H group which is capable of being nitrosated.