100169-40-2Relevant academic research and scientific papers
3-Aryltetronic acids: Efficient preparation and use as precursors for vulpinic acids
Mallinger, Aurelie,Gall, Thierry Le,Mioskowski, Charles
, p. 1124 - 1129 (2009)
3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphe-nyl) tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester and the dehydration of the tertiary alcohols obtained into mixtures of (E)-and (Z)-alkenes, which were converted under UV irradiation at 254 nm to natural (E)-isomers. Syntheses of pinastric acid, 4,4′-dimethoxyvulpinic acid, and the first synthesis of recently isolated methyl 3′,5′-dichloro-4,4′-di-0-methylatromentate were hence achieved in an efficient manner.
