Solanidan-2,3-diol

Hydrogen peroxide and peracids react with solanidine acetate, with solanidan-3/3-ol, or with solanidane to yield JV-oxides, which on treatment with sulfur dioxide regenerate the starting material. With one mole of perbenzoic acid, A -solanidene yields an W-oxide but with two moles of the reagent it yields a 2,3-epoxide-JV-oxide, which on treatment with sulfur dioxide generates a diol, probably solanidan-2,3-diol (15, 45, 57). 

Another route by which rubijervine is convertible into known solanidine derivatives is by way of the saturated diol V, which was first oxidized with chromic acid in acetic acid to the diketone (XIV), the bis(semi-carbazone) of which on Wolff-Kischner reduction afforded a mixture of 3/3-solanidanol (IX, p. 256) and solanidane (V, p. 256) (57). Dehydrogenation of rubijervine with selenium gave the typical dehydrogenation... 

---