Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. I. The Grignard Reaction of 5-(2-Methyl-1,3-dioxo-2-cyclopentyl) methyl-2,5H-furanone with Isopropenylmagnesium Bromide and Stereochemistries of the Products
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概要
- 論文の詳細を見る
1,6-Addition of 2-methyl-1,3-cyclopentanedione (8) to protoanemonin (7) gave 5-(2-methyl-1,3-dioxo-2-cyclopentyl) methyl-2,5H-furanone (6). The Grignard reaction of 6 with isopropenylmagnesium bromide-cuprous iodide provided two kinds of lactones, (10) and (11), in excellent yield through 1,4-addition of the Grignard reagent to 6 and the subsequent internal aldol cyclization. These lactones, however, possessed the undesired stereostructures for the present synthesis and conversion of the lactone (10) into the desired lactone (4) was performed by retroaldol cleavage and subsequent internal aldol recyclization as shown in Chart 6.
- 社団法人日本薬学会の論文
- 1983-06-25
著者
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内山 文昭
Faculty Of Pharmaceutical Sciences Kyoto University
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犬伏 康夫
Faculty of Pharmaceutical Sciences, Kyoto University
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田中 圭
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
静岡県大 薬
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古澤 康秀
Faculty Of Pharmaceutical Sciences Kyoto University
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浅田 與
Faculty of Pharmaceutical Sciences, Kyoto University
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犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
京都大学薬学部
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浅田 與
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
Faculty of Eng., Oita Univ.
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