2,2-Dimethylsuccinic acid derivatives in isoprenoid synthesis: a 2,2-dimethylvinyl anion equivalent in the synthesis of ar-atlantone, ar-turmerone, and prenylated aromatic compounds

The anion of methyl 2,2-dimethylsuccinate was alkylated with benzylic bromides to give the corresponding 3-substituted-2,2-dimethylsuccinates. Hydrolysis to the dicarboxylic acids, followed by bisdecarboxylation with lead tetraacetate, afforded 1-aryl-3-methyl-2-butenes, which are model prenylated a...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 70; no. 5; pp. 1317 - 1322
Main Authors Strunz, George M, Ya, Li
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.05.1992
Natl Research Council Canada
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:The anion of methyl 2,2-dimethylsuccinate was alkylated with benzylic bromides to give the corresponding 3-substituted-2,2-dimethylsuccinates. Hydrolysis to the dicarboxylic acids, followed by bisdecarboxylation with lead tetraacetate, afforded 1-aryl-3-methyl-2-butenes, which are model prenylated aromatic compounds. Acylation of methyl 2,2-dimethylsuccinate with E-3-(4′-methylphenyl) crotonyl chloride gave the substituted succinate 9 . Hydrolysis of the ester groups and acid-catalyzed decarboxylation of the resulting β-ketoacid produced the keto acid 10 , which was decarboxylated by the Kochi method, furnishing ar-atlantone. Hydrogenation of 10 yielded 12 , which on similar decarboxylation afforded ar-turmerone.
ISSN:0008-4042
1480-3291
DOI:10.1139/v92-169