Enantioselective synthesis of a key intermediate of 20(S)-camptothecin via an enzyme-catalyzed resolution.
The key intermediate of a 20(S)-camptothecin 1 synthesis was obtained in a highly enantioselective fashion using an enzyme-catalyzed resolution. A commercially available protease was found to exhibit the highest enantioselectivity with moderate activity, and (S)-ethyl 2-acetoxy-2-[6-(acetoxymethyl)-1,1-(ethylenedioxy)-5-oxo- 1,2,3,5-tetrahydroindolizin-7-yl]butanoate 7c of 98% e.e. was obtained as the remaining substrate.
Imura
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A
Chemical Technology Research Laboratories, Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan.
Itoh
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M
Miyadera
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D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D010450:Endopeptidases / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000970:Antineoplastic Agents; D010450:Endopeptidases; D002166:Camptothecin