6125-52-6Relevant academic research and scientific papers
A New Synthesis of a Naturally Occuring Isocoumarin. 3,4-Dimethyl-8-hydroxyisocoumarin (Oospolactone)
Singh, Hardeo N.,Singh, Ramayan Prasad
, p. 685 - 687 (2007/10/02)
3,4-Dimethyl-8-methoxyisochroman (5a) on oxidation furnishes 3,4-dimethyl-8-methoxy-3,4-dihydroisocoumarin (6a), and demethylated with hydriodic acid to 3,4-dimethyl-8-hydroxy-3,4-dihydroisocoumarin (7a).Treatment of 6a with N-bromosuccinimide followed by refluxing with triethylamine furnishes 3,4-dimethyl-8-methoxyisocoumarin (8a) which on demethylation with hydriodic acid yields 3,4-dimethyl-8-hydroxyisocoumarin (oospolactone) (9a).Compound 5a and 3,4-dimethyl-6-methoxyisochroman (5b) obtained by treating 3-(m-methoxyphenyl)butan-2-ol (4) with HCHO/HCl are separated by fractional distillation.Compound 4 is obtained from α-(m-methoxyphenyl)propionaldehyde (3) by Grignard reaction with methylmagnesium iodide.The aldehyde (3) is obtained from m-methoxyacetophenone (1) by Darzens glycidic ester condensation followed by hydrolysis and decarboxylation of the resulting product.
A New Synthesis of Tetrahydrocapillarine, O-Methylglomelline and Oospolactone
Chatterjea, Jnanendra N.,Mukherjee, Sanat K.,Bhakta, Chittaranjan,Jha, Hem Chandra,Zilliken, Fritz
, p. 3927 - 3931 (2007/10/02)
Pyridine catalysed acylation of a number of homophthalic acids with various acid anhydrides has been extensively studied, leading to the synthesis of several substituted isocoumarins including the natural products mentioned above.
