Studies on Digitalis Glycosides. XV. The Structure of Purpnigenin. (2).
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概要
- 論文の詳細を見る
The Oppenauer oxidation product (II) of purpnigenin (I) was assumed to be 14,15-dihydroxyprogesterone and, therefore, two kinds of 14,15-dihydroxy compound (VI and VIII) were synthesized from progesterone (III) to compare with (II). Oxidation of ⊿^<14>-progesterone (V) with osmium tetroxide produced 14α, 15α-dihydroxyprogesterone (VI) which did not agree with (II). Oxidation of (V) with peracid and cleavage of the epoxide thereby obtained with perchloric acid produced 14,15-dihydroxypregn-4-ene-3,20-dione (VIII) which was identified with (II). This has proved that (II) is 4-pregnene-14,15-Consequently, the original purpnigenin is considered to be 3,14,15-trihydroxypregn-5-en-20-one. The two hydroxyls at 14-and 15-positions are considered to be trans-diols but further examination will have to be made as to their exact configuration. It is interesting that pregnenolone, hitherto considered as animal constituent, has now been found in a plant as an aglycone.
- 公益社団法人日本薬学会の論文
- 1962-05-25
著者
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石井 宏
Research Laboratory, Shionogi & Co., Ltd.
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石井 宏
Shionogi Research Laboratories Shionogi & Co. Ltd.
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