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Enantioselective Total Synthesis of (+)-Conicol via Cascade Three-Component Organocatalysis

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posted on 19.02.2010, 00:00 by Bor-Cherng Hong, Prakash Kotame, Chih-Wei Tsai, Ju-Hsiou Liao
The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael−Michael−Michael−aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and α,β-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.