Enantiopure isoplagiochin C by directed deracemization through axis-to-axis chirality transfer |
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Authors: | Gerhard Bringmann Dominik Hager Anu Schaumlöffel Matthias Groh Andreas Speicher |
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Affiliation: | 1. Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany;2. FR 8.1 Chemistry, Organic Chemistry, Saarland University, 66041 Saarbrücken, Germany |
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Abstract: | Isoplagiochin C 1 was prepared for the first time in enantiopure form from synthetic racemic material, using a novel stereochemical concept. This macrocyclic bisbibenzyl contains two biaryl axes. Of these, axis A is configurationally stable by its fixation within the macrocyclic framework, while axis B is stereochemically unstable. By diesterification of rac-1 with enantiopure (P)-1,1′-binaphthyl-2,2′-dicarboxylic acid, axis B is locked in its P-configuration, thus allowing the resolution and separate saponification of dilactones (PA,PB,P)-3 and (MA,PB,P)-3 to give the pure enantiomers of 1. This concept permits recycling of any undesired enantiomer of 1 by thermal equilibration of the respective diastereomer of 3. |
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