TRANSFORMATIONS OF SOLASODINE

Article abstract of DOI:10.1007/BF00567292

Solasodine (I) has been subjected to a number of transformations.The following compounds have been obtained from it by described procedures: 3β-acetoxypregna-5,16-dien-20-one (II), 3β-acetoxypregn-5-en-20α-ol (III), and 3β-acetoxypregn-5-en-20β-ol (IV).The oxidation of (III) and (IV), the formation of an oxime, and the reduction of the oxime with sodium in ethanol, followed by Hess methylation, has led to 20α-dimethylaminopregn-5-en-3β-ol (IX) and to 20β-dimethylaminopregn-5-en-3β-ol (X).From compounds (IX) and (X), by analogy with (III) and (IV) by their oxidation and the preparation of oximes, which were then reduced and methylated, the following were obtained: 3β,20α-bisdimethylaminopregnane (XVII) and 3β,20β-bisdimethylaminopregnane (XVIII), and also quaternary salts of the latter.