Studies on Acetylenic Compounds. XLII. Total Synthesis of Estrone by the Double Cyclization of Acetylenic Compounds
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概要
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Total synthesis of estrone by the double cyclization of an acetylenic compound was achieved. This method consists of building up B and C rings of the steroidal skeleton in one step starting from a compound having A and D rings of the future steroidal system. Actually treatment of 2-methyl-2-[6-(m-methoxyphenyl)-2-hexynyl]-1,3-cyclopentanedione (XII) with polyphosphoric acid successfully gave 3-methoxyestra-1,3,5 (10), 8,14-pentaen-17-one (XIII)which is a key intermediate to estrone, whereas this type of the double cyclization of a symmetrically disubstituted acetylenic compound, 1,6-bis (m-methoxyphenyl)-3-hexyne (XIII), proceeded in a different way giving the undesirable tetracyclic spirane derivative (IV).
- 公益社団法人日本薬学会の論文
- 1966-03-25
著者
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岩井 一成
Central Research Laboratories, Sankyo Co., Ltd.
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平岡 哲夫
Central Research Laboratories, Sankyo Co., Ltd.
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平岡 哲夫
三共(株)総合研究所
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岩井 一成
Central Research Laboratories Sankyo Co. Ltd.
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