144782-33-2Relevant academic research and scientific papers
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
Strunz, George M.,Ya, Li
, p. 1317 - 1322 (2007/10/02)
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.Hydrogenatio n of 10 yielded 12, which on similar decarboxylation afforded ar-turmerone.
