Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system: an application to the synthesis of alkaloids 223A and 205B from poison frogs |
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Authors: | Naoki Toyooka Ayako Fukutome |
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Institution: | Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-0194, Japan |
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Abstract: | Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system has been achieved by sequential stereocontrolled Michael-type conjugate addition reaction of appropriate enaminoesters. This methodology has been applied to the total syntheses of the poison frog alkaloids 223A and 205B. The relative stereochemistry of natural 223A at the 6-position was revised, and the absolute stereochemistry of natural 205B was determined by the present synthesis. |
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Keywords: | Alkaloids Comins' triflating agent Piperidones |
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