Studies on the Total Synthesis of dl-Colchiceine. II. Synthesis of dl-Demethoxydeoxyhexahydrocolchiceine.
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概要
- 論文の詳細を見る
Demethoxydeoxyhexahydrocolchlicine (XX), one of the decomposition products of colchicine was synthesized. 1-O-Methylpyrogallol was derived to 3-methoxyl-4-hydroxy-8,9,10,11-tetrahydrobenzo [b] cyclohepta [d] pyran-6-one (IV) and to methyl 2-[6-(2-methoxy-carbonylethyl)-2,3,4-trimethoxyphenyl]-1-cycloheptenecarboxylate (XIV) via the 1-formyl compound (VIII) and 1-(2-carboxyethyl) compound (XII) of (VI), and Dieckmann condensation of (XIV) gave 1,2,3-trimethoxy-5,6,10,12-hexahydrobenzo [a] heptalen-7 (8H)-one, which was also obtained by dehydrative condensation of the free acid (XIII) of (XIV). (III) was derived to its oxime which was reduced and acetylated to dl-7-acetamido-1,2,3-trimethoxy-5,6,7,8,9,10,11,12-octahydrobenzo [a] heptalene (XIX) whose double bond was rearranged to form the racemic compound of (XX). The position of the double bond in (XX) was determined. dl-N-formyldeacetyldemethoxydeoxyhexahydrocolchicine (XXI) was obtained in one step from (III) by the Leuckart reaction.
- 社団法人日本薬学会の論文
- 1962-04-25
著者
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砂川 玄俊
Central Research Laboratories Sankyo Co. Ltd.
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砂川 玄俊
Takamine Research Laboratory Sankyo Co. Ltd.
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中沢 準一
Central Research Laboratories, Sankyo Co., Ltd.
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中村 隆洋
Takamine Laboratory, Sankyo Co., Ltd.
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中沢 準一
Takamine Laboratory, Sankyo Co., Ltd.
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中村 隆洋
Takamine Laboratory Sankyo Co. Ltd.
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中沢 準一
Central Research Laboratories Sankyo Co. Ltd.
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- Studies on the Total Synthesis of dl-Colchiceine. II. Synthesis of dl-Demethoxydeoxyhexahydrocolchiceine.
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- 28 コルヒチンの完全合成
- Studies on the Total Synthesis of dl-Colchiceine. III.
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