ビスデヒドロジヒドロエンメインの熱分解物の合成 : 第1報 6-Hydroxy-7-methylphthalideおよび2-Hydroxymethyl-6,6-dimethyl-5-oxo-1-cyclohexenecarboxylic Acid Lactoneの合成
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概要
- 論文の詳細を見る
In the course of an investigation on the structure of enmein (I), isolated from Isodon trichocarpus, five well-characterized products (IV-VIII) were obtained by pyrolysis of bisdehydrodihydroenmein (II). In the present paper, synthesis of two (V and VI) of those compounds which obviously originated from ring A of compound (II) is reported. The former compound, 6-hydroxy-7-methylphthalide (V), was prepared in the following way. Chloromethylation of m-methoxybenzoic acid under the forcing conditions gave a mixture of compounds consisting of X, XI, and XII which were separated by fractional crystallization. Hydrogenation of XI followed by treatment with hydriodic acid yielded V, identical with one of the pyrolysis products mentioned above. The latter compound (VI) was synthesized by two alternative methods. First, compound (XXII) was treated with thionyl chloride to give XXIII which was then subjected to bromination, followed by sodium borohydride reduction, giving XXXI. The resulting XXXI was subsequently dehydrobrominated to give XXXII, which on oxidation, followed by C-methylation, gave a compound which was identical with VI. The other method used to produce VI involves first the addition of dimethyl acetylenedicarboxylate to butadiene. The resulting diester (XLVII) was converted to the anhydride (XLVIII) and then reduced with lithium aluminum hydride, giving XLIX. Treatment of this with NBS yielded LII which was debrominated by treatment with Raney Ni. The resulting hydroxy-lactone (LIII) was oxidized and then C-dimethylated to yield VI.
- 公益社団法人日本薬学会の論文
- 1968-09-25
著者
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入江 寛
Faculty Of Pharmaceutical Sciences Kyoto University
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上尾 庄次郎
京都大学薬学部
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入江 寛
京都大学薬学部
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沼田 敦
Osaka College Of Pharmacy
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沼田 敦
京都大学薬学部
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大野 孝正
京都大学薬学部
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大野 孝正
Faculty of Pharmaceutical Sciences Kyoto University
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