Synthesis of (±)-kigelin
A simple synthesis of racemic 8-hydroxy-6,7-dimethoxy-3-methyl-3,4-dihydroisocoumarin or kigelin, a metabolite of Aspergillus terreus and Kigelia pinnata, exhibiting several bioactivities, is described. 3,4,5-Trimethoxyhomophthalic acid was refluxed with acetic anhydride in dry pyridine to afford 2,3,4-trimethoxy-6-(2-oxopropyl)benzoic acid. Reduction of the latter followed by cyclodehydration yielded 6,7,8-trimethoxy-3-methyl-3,4-dihydroisocoumarin which on regioselective demethylation furnished the (±)-kigelin.
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2005
|
| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000500010 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|