An efficient total synthesis of trilepisiumic acid.
Total synthesis of trilepisiumic acid (4-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-3-hydroxybenzoic acid) isolated from Trilepisium madagascariense was carried out. Doebner condensation of 3,4-dimethoxybenzaldehyde with malonic acid yielded 3,4-dimethoxycinnamic acid (2). Esterification of the latter with vanillin afforded 4-formyl-2-methoxyphenyl-3-(3,4-dimethoxy phenyl)acrylate (3) followed by permanganate oxidation in acidic medium provided the corresponding acid 4. Finally, demethylation of 4 was achieved by refluxing in hydrobromic acid to unveil the trilepisiumic acid (1).
a Department of Chemistry , Quaid-I-Azam University , Islamabad 45320 , Pakistan.
Aamer
A
Saeed
Muhammad
M
Qasim
D001547:Benzaldehydes / Q000737:chemistry; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D029586:Moraceae / Q000737:chemistry*; D014197:Trees / Q000737:chemistry
D001547:Benzaldehydes; D001565:Benzoates; D062385:Hydroxybenzoates; C000592646:trilepisiumic acid; C427725:veratraldehyde
Trilepisium madagascariense; cinnamic acid; trilepisiumic acid