- Lipase-catalyzed enantioselective hydrolysis of bis(acyloxymethyl) 1,4- dihydro-3,5-pyridinedicarboxylates leading to optically active medicines
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Chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates and 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase catalyzed hydrolysis of bis(acyloxymethyl) 1,4-dihydro- 3,5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.
- Ebiike, Hirosato,Maruyama, Kaori,Yamazaki, Yukiyoshi,Hirose, Yoshihiko,Kariya, Kinya,Sasaki, Ikuharu,Kurono, Yoshiaki,Terao, Yoshiyasu,Achiwa, Kazuo
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p. 863 - 868
(2007/10/03)
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- Lipase-catalyzed asymmetric hydrolysis and regioselective bromination of 1,4-dihydropyridine. Synthesis of (R)-(+)-nilvadipine
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Homochiral (R)-(+)-nilvadipine was synthesized from a prochiral substrate using lipase-catalyzed asymmetric hydrolysis and subsequent regioselective bromination as key steps.
- Ebiike,Achiwa
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p. 1447 - 1450
(2007/10/02)
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- Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines
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Two enantiomers of 1,4-dihydropyridine compounds have been obtained with high enantiomeric purity by lipase-catalyzed hydrolysis in organic solvent saturated with water. Enantioselectivity of this reaction is dependent on the solvent used.
- Hirose, Yoshihiko,Kariya, Kinya,Sasaki, Ikuharu,Kurono, Yoshiaki,Ebiike, Hirosato,Achiwa, Kazuo
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p. 7157 - 7160
(2007/10/02)
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- Acyloxymethyl as an activating group in lipase-catalyzed enantioselective hydrolysis. A versatile approach to chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates
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The first practical syntheses of chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates, which are attractive compounds as new calcium antagonists, were realized by lipase-catalyzed enantioselective hydrolysis of the acyloxymethyl esters. The monoesters obtained were revealed to have high optical purity and demonstrated to be useful chiral synthons.
- Ebiike,Terao,Achiwa
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p. 5805 - 5808
(2007/10/02)
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