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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.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 10 (5), 354-357, 1962
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204174432512
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- NII論文ID
- 110003618861
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可