Heterocyclic Prostaglandins. II. An Effective Synthesis of 3,7-Dioxabicyclo [3.3.0] octane-2,8-dione and Its C_1-Substituted Derivatives
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概要
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New dilactones (2a-j, 3a, and 3b) having a 3,7-dioxabicyclo [3.3.0] octane-2,8-dione system (1f) have been prepared starting from diethyl 2-formyl succinate (5). Treatment of a 2-ethoxycarbonyl-3-hydroxymethyl-4-butanolide derivative (9) with acidic ethanol gave 3,7-dioxabicyclo [3.3.0] octane-2,8-dione (2a). Alkylation of 2a with various alkyl halides gave C_1-substituted-3,7-dioxabicyclo [3.3.0] octane-2,8-diones (2b-g) in moderate yields. The same compounds (2b-g) were also prepared from 9 after alkylation followed by acid treatment. 1-(6-Methoxycarbonyl-2-hexynyl)-3,7-dioxabicyclo [3.3.0] octane-2,8-dione (2h) and the 1-(6-cyano-2-hexynyl) analog (2i) were also prepared from 9. Partial hydrogenation of the acetylenic derivatives (2h and 2i) gave the corresponding cis-olefinic compounds (3a and 3b), which are potential synthetic intermediates for 10-oxa-11-deoxyprostaglandin E_2 (4).
- 社団法人日本薬学会の論文
- 1979-10-25
著者
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石田 昭彦
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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野口 勝通
田辺製薬株式会社有機化学研究所
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和田 征夫
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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日水 順一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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