On the Absolute Configuration of Natural 24-Alkylsterols.
スポンサーリンク
概要
- 論文の詳細を見る
(+)-Limonene (I) was converted to (+)-trans-p-methane-1,2-diol (III) via dihydrolimonene (II) by known methods. (III) was converted to (+)-3-isopropyl-6-oxoheptanoic acid (VI), either by direct oxidation of (III) with Lemieux reagent or by two-step oxidation via keto-aldehyde, 3-isopropyl-6-oxoheptanal (V). (VI) was, in turn, converted to its (+)-ester (VIII), (+)-ketal-alcohol (X), ketal-alcohol tosylate (XI) and finally to a levorotatory ketone, 5-isopropyl-2-heptanone (XII). Since the (-)-ketone (XII) has the same absolute configuration around its asymmetric carbon as (+)-limonene (I), (XII) must be (-)-(S)-5-isopropyl-2-heptanone, corresponding to the 24β-ethyl in the steroid-chain. The antipode of (XII), (+)-(R)-ketone (XII'), has already been obtained directly from β-sito-sterol by Dirscherl and Nahm. Hence the ethyl group of the stigmasterol series must have α-configuration in the extended Plattner's convention proposed by Fieser and Fieser. This result confirmed the recent conclusion which contradicted the deduction Bergmann and others. The author proposes the revision of the older representation of C_<29>-natural sterols in regard to the C-24 configurations.
- 公益社団法人日本薬学会の論文
- 1960-04-25
著者
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岸田 有吉
Central Research Laboratories Sankyo Co. Ltd.
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岸田 有吉
Takamine Research Laboratory Sankyo Co. Ltd.
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