Diosgenin is a close relative of cholesterol. The structural difference lays on the incorporation of a...

Diosgenin is a close relative of cholesterol. The structural difference lays on the incorporation of a spyroketal group on diosgenin. Propose how this functional group is obtained.

Expert Solution

Cholesterol on the hydrolysis of the C-26 and then at C-16 leads to the formation of the hydroxyl groups on the cholesterol and then laterally the group is transfer for attaining the stability of the structure. Further the nucleophilic attack by the lone pair of the electrons present on the oxygen molecule and then through the effect of tautomerization the hydroxyl group is converted into the keto group. This ketone group is formed on the C-16 and then on the chemical hydrolysis again the cyclic bond formation takes place which lead to the spiroketal structure and lead to the synthesis of the diosgenin from the cholesterol. For the actual mechanism follow the given mechanism in structure:

gladiator answered 2 years ago

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