High-pressure Diels-Alder approach to natural kainic acid |
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Authors: | Pandey Sushil K Orellana Arturo Greene Andrew E Poisson Jean-François |
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Institution: | Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France. |
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Abstract: | The first Diels-Alder based synthesis of (-)-kainic acid is described. Danishefsky's diene and a vinylogous malonate derived from 4-hydroxyproline combine under high pressure to afford a key bicyclic intermediate with virtually no loss of enantiopurity. This adduct can be converted into the natural product with complete stereocontrol. reaction: see text]. |
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