Enzymatic Optical Resolution of Dibenzoxepins and Its Application to an Optically Active Antiallergic Agent with Thromboxane A2Receptor Antagonistic Activity
Copyright policy )Enzymatic Optical Resolution of Dibenzoxepins and Its Application to an Optically Active Antiallergic Agent with Thromboxane A2Receptor Antagonistic Activity
Methyl (+/-)-11-(2-hydroxyethyl)thio-6,11-dihydrodibenz[b,e]oxepin- 2- carboxylate (5) was enantio-selectively acylated with acetic anhydride in an organic medium by Lipase Amano P to give methyl (-)-11-(2-acetoxyethyl)thio-6,11-dihydrodibenz[b,e]oxepin-2- carboxylate (8), and the (+)-enantiomer by Lipase Sigma Type VII. Using Lipase Amano P, (+)- and (-)-(5) could be prepared with high optical purity (84-94% e.e.). These products were respectively converted to (+)- and (-)-KW-4099, which had antiallergic activity with complete retention of the optical purity.
Thromboxane A2, Magnetic Resonance Spectroscopy, Piperidines, Spectrophotometry, Infrared, Acylation, Hydrolysis, Receptors, Thromboxane, Stereoisomerism, Chromatography, High Pressure Liquid, Dibenzoxepins
Thromboxane A2, Magnetic Resonance Spectroscopy, Piperidines, Spectrophotometry, Infrared, Acylation, Hydrolysis, Receptors, Thromboxane, Stereoisomerism, Chromatography, High Pressure Liquid, Dibenzoxepins
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