Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora
Open Access
- 31 March 2011
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 2 (1), 117-119
- https://doi.org/10.5155/eurjchem.2.1.117-119.201
Abstract
The synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one (1) isolated from the stem and root bark extracts of Tessmannia densiflora has been described. The reaction of 3,5-dimethoxyhomophthalic anhydride (2) with hexanoyl chloride in the presence of 1,1,3,3-tetramethylguanidine and triethylamine afforded 6,8-dimethoxy-3-pentylisocoumarin (3). Regioselective demethylation of the latter using anhydrous aluminum chloride furnished the title isocoumarin (1).Keywords
This publication has 15 references indexed in Scilit:
- Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from TessmanniadensifloraPhytochemistry, 2009
- Bioactive Isocoumarins Isolated from the Endophytic Fungus Microdochium bolleyiJournal of Natural Products, 2008
- Synthesis of 6-O-methyl ether of Scorzocreticin and Scorzocreticoside I, metabolites from Sorzonera creticaJournal of Asian Natural Products Research, 2006
- Sg17-1-4, a Novel Isocoumarin from a Marine Fungus Alternaria tenuis Sg17-1The Journal of Antibiotics, 2006
- Synthesis of (±)-kigelinJournal of the Brazilian Chemical Society, 2005
- From Traditional Biomarkers to Transcriptome Analysis in Drug DevelopmentCurrent Molecular Medicine, 2005
- Synthesis of 6,8-Dihydroxy-3-(2′-Acetyl-3′, 5′-Dihydroxyphenyl)Methylisocoumarin Related to FeralolideNatural Product Research, 2004
- Intestinal Anti-Inflammatory Activity of Paepalantine, an Isocoumarin Isolated from the Capitula ofPaepalanthus bromelioides, in the Trinitrobenzenesulphonic Acid Model of Rat ColitisPlanta Medica, 2004
- Stereoselective Synthesis of (3R)-3,4-Dihydro-6,8-dimethoxy-3-undecyl- 1H-[2]benzopyran-1-one and Derivatives, Metabolites from Ononis natrixHelvetica Chimica Acta, 2003
- Metabolites from Fungi 15. New Isocoumarins from an Endophytic Fungus Isolated from the Canadian ThistleCirsium arvenseNatural Product Letters, 2001