Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines

Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines

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 chira...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1997/05/15, Vol.45(5), pp.863-868
Hauptverfasser: EBIIKE, Hirosato, MARUYAMA, Kaori, YAMAZAKI, Yukiyoshi, HIROSE, Yoshihiko, KARIYA, Kinya, SASAKI, Ikuharu, KURONO, Yoshiaki, TERAO, Yoshiyasu, ACHIWA, Kazuo
Format: Artikel
Sprache:eng
Schlagworte:
1, 4-dihydropyridine
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
calcium antagonist
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
lipase-catalyzed reaction
Methods. Procedures. Technologies
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.45.863