Conversion of spirostane and solanidane into pregnane (1)introduction of oxygen function into C-23 |
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Authors: | Nakata Nodoka Tokudome Asami Yanai Hiroyuki Nohara Toshihiro |
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Institution: | Faculty of Medical and Pharmaceutical Scieces, Sojo University, 4-22-1 Ikeda, Kumamoto 860-0082, Japan. |
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Abstract: | A spirosolane derivative possessing a hydroxyl group at C-23, esculeogenin A, a sapogenol of tomato saponin, was found to be easily converted into the corresponding pregnane derivative by refluxing with aqueous pyridine. Therefore, introduction of a hydroxyl group into the C-23 of diosgenin (as representative of spirostane derivatives) and solasodine (as representative of spirosolane derivatives) was attempted by the reaction of NaNO(2)-BF(3)?·?Et(2)O. In diosgenin, the objective compound was obtained by the reaction in AcOH. However, in solasodine, we obtained a 23-nitroso derivative by the reaction in AcOH and 23,24-bisnorcholanic acid 22-16 lactone, or vespertilin, in AcOH and CHCl(3). |
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