Synthetic Studies on the Lycopodium Alkaloids. IV. : Total Synthesis of dl-Anhydrolycodoline and dl-Lycopodine
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概要
- 論文の詳細を見る
The total synthesis of dl-anhydrolycodoline is reported. The amino-ketone (3), obtained from the amine (4) in four steps, was treated with acrylyl chloride to give the amide (1). Unfortunately, the intramolecular Michael-type cyclization of 1 to the lactam (9) for lycodoline did not take place for a stereoelectronic reason. Dehydration of 1 with conc. sulfuric acid afforded the anhydro-amide (10), which was cyclized in the presence of sodium ethoxide and dicyclohexyl-18-crown-6 to give the tetracyclic lactam (11) in a moderate yield. Reduction of 11 with lithium aluminum hydride followed by oxidation with Jones reagent afforded dl-anhydrolycodoline.
- 公益社団法人日本薬学会の論文
- 1978-10-25
著者
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金 相元
Faculty of Pharmaceutical Sciences, Josai University
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金 相元
Faculty Of Pharmaceutical Sciences Josai University
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堀井 善一
Faculty Of Pharmaceutical Sciences Josai University
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堀井 善一
Faculty Of Pharmaceutical Sciences Osaka University
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坂東 幸英
Faculty Of Pharmaceutical Sciences Josai University
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高橋 延子
Faculty Of Pharmaceutical Sciences Josai University
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