Total Synthesis of 12α- and 12β-Carboxylated Estrogens via the Thermal Elimination of β-Ketosulfoxide(Organic,Chemical)
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概要
- 論文の詳細を見る
The thermal elimination of β-ketosulfoxide (2) afforded the α,β-unsaturated γ-ketoester (3) as a Michael acceptor (analogous to the key intermediate in Smith's estrone synthesis), which was condensed with 2-methylcyclopentane-1,3-dione to give the adduct (4) having all carbon units of the aromatic steroidal skeleton. The Michael adduct was then cyclized in the presence of methanesulfonic acid to yield the novel estrapentaene (6) with a methoxycarbonyl group at the C-12 position. The estrapentaene (6) was converted to 12β- and 12α-methoxycarbonylestrones (25 and 26) and their estradiol derivatives (27 and 28) by selective reductions followed by demethylation.
- 公益社団法人日本薬学会の論文
- 1987-02-25
著者
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黒澤 隆夫
北海道大学医学部附属病院 検査部
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藤間 貞彦
Faculty Of Pharmaceutical Sciences Higashi Nippon Gakuen University
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Kurosawa T
Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido
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Kurosawa Takao
Health Sci. Univ. Hokkaido Hokkaido Jpn
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黒澤 隆夫
Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido
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新津 宇田子
Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University
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新津 宇田子
Faculty Of Pharmaceutical Sciences Higashi-nippon-gakuen University
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