Synthesis of 6,8-dihydroxy-3-(2'-acetyl-3',5'-dihydroxyphenyl)methylisocoumarin related to feralolide.
Base-catalyzed self-condensation of 3,5-dimethoxyhomophthalic acid (2) directly furnished the 6,8-dimethoxy-3-(2'-carboxy-3',5'-dimethoxyphenyl)methylisocoumarin (3) which on successive treatment with oxalyl chloride, diazomethane and hydrolysis afforded the corresponding 2'-acetylisocoumarin (5). Complete demethylation of the latter yielded the 6,8-dihydroxy-3-(2'-acetyl-3',5'-dihydroxyphenyl)methylisocoumarin (6) related to the natural product feralolide (1a).
Saeed
Aamer
A
Department of Chemistry, Quaid-i-Azam University 45320, Islamabad, Pakistan.
D000504:Aloe; D003374:Coumarins / Q000737:chemistry*; D006801:Humans; D049934:Isocoumarins; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry*
C489879:6,8-dihydroxy-3-(2'-acetyl-3',5'-dihydroxyphenyl)methylisocoumarin; D003374:Coumarins; D049934:Isocoumarins; D010936:Plant Extracts; D012118:Resorcinols