Potential Bile Acid Metabolites. 25. Synthesis and Chemical Properties of Stereoisomeric 3α, 7α, 16- and 3α, 7α, 15-Trihydroxy-5β-cholan-24-oic Acids
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概要
- 論文の詳細を見る
Epimeric 3α, 7α, 16- and 3α, 7α, 15-trihydroxy-5β-cholan-24-oic acids and some related compounds were synthesized from chenodeoxycholic acid (CDCA) and ursodeoxycholic acid (UDCA), respectively. The key reaction involved one-step remote oxyfunctionalization of unactivated methine carbons at C-17 of CDCA and at C-14 of UDCA as their methyl ester-peracetate derivatives with dimethyldioxirane (DMDO). After dehydration of the resulting 17α- and 14α-hydroxy derivatives with POCl_3 or conc. H_2S0_4, the respective Δ^16- and Δ^14-unsaturated products were subjected to hydration via hydroboration followed by oxidation to yield the 3, 7, 16- and 3, 7, 15-triketones, respectively. Stereoselective reduction of the respective triketones with tert-butylamine-borane complex afforded the epimeric 3α, 7α, 16- or 3α, 7α, 15-trihydroxy derivatives exclusively. A facile formation of the corresponding ε-lactones between the side chain carboxyl group at C-24 and the 16α- (or 16β-) hydroxyl group in bile acids is also clarified.
- 社団法人日本薬学会の論文
- 2002-10-01
著者
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Mano Nariyasu
Dep. Of Pharmaceutical Sciences Tohoku Univ. Hospital
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Mano Nariyasu
東北大学 薬研究
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Mano N
Tsukuba Research Laboratories Eisai Co. Ltd.
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Mano Nariyasu
Graduate School Of Pharmaceutical Sciences Tohoku University
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GOTO Junichi
Graduate School of Pharmaceutical Science, Tohoku University
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Goto J
Tohoku Univ. Sendai Jpn
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Goto J
The Ion Engineering Research Institute Corporation
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Iida Takashi
Dep. Of Chemistry Coll. Of Humanities & Sciences Nihon Univ.
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Mano N
Dep. Of Pharmaceutical Sciences Tohoku Univ. Hospital
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Kakiyama Genta
Dep. Of Chemistry Coll. Of Humanities & Sciences Nihon Univ.
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NAMBARA Toshio
Graduate School of Pharmaceutical Sciences, Tohoku University
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IIDA Takashi
College of Humanities and Sciences, Nihon University
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HIKOSAKA Masahiro
College of Humanities and Sciences, Nihon University
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KAKIYAMA Genta
College of Humanities and Sciences, Nihon University
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SHIRAISHI Keisuke
College of Humanities and Sciences, Nihon University
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SCHTEINGART Claudio
Department of Medicine, University of Calfornia
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HAGEY Lee
Department of Medicine, University of Calfornia
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TON-NU Huong-Thu
Department of Medicine, University of Calfornia
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HOFMANN Alan
Department of Medicine, University of Calfornia
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Goto J
Division Of Clinical Pharmacy Graduate School Of Pharmaceutical Sciences Tohoku University
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Mano Nariyasu
Analytical Chemistry And Pharmaceutical Research Section Tsukuba Research Laboratories Eisai Co. Ltd
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Hagey Lee
Department Of Medicine University Of Calfornia
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Hofmann Alan
Department Of Medicine University Of Calfornia
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Nambara T
Tohoku Univ. Sendai Jpn
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Nambara T
Graduate School Of Pharmaceutical Sciences Tohoku University
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Hasegawa Maki
Fac. Of Pharmaceutical Sciences Kinki Univ.
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Schteingart Claudio
Department Of Medicine University Of Calfornia
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Shiraishi Keisuke
Department Of Chemistry College Of Humanities & Sciences Nihon University
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Ton-nu Huong-thu
Department Of Medicine University Of Calfornia
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Goto Junichi
Graduate School Of Pharmaceutical Science Tohoku University
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Goto Junichi
Department of Pharmaceutical Sciences, Tohoku University Hospital
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