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High-pressure Diels-Alder approach to natural kainic acid
Sushil K Pandey1, Arturo Orellana, Andrew E Greene
1Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France.
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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