Published July 2005
| Version v1
Journal article
Synthesis of (±)-kigelin
Creators
- 1. Quaid-I-Azam University, Islamabad (Pakistan). Dept. of Chemistry
Description
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. (author)
Availability note (English)
Available from http://www.scielo.br/pdf/jbchs/v16n4/25347.pdfAdditional details
Identifiers
Publishing Information
- Journal Title
- Journal of the Brazilian Chemical Society
- Journal Volume
- 16
- Journal Issue
- 4
- Journal Page Range
- p. 739-742
- ISSN
- 0103-5053
- CODEN
- JOCSET
INIS
- Country of Publication
- Brazil
- Country of Input or Organization
- Brazil
- INIS RN
- 38093436
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Descriptors DEI
- BENZOIC ACID; BORON; CARBON 13; COUMARIN; ETHYL RADICALS; HYDROGEN 1; INFRARED SPECTRA; LIQUID COLUMN CHROMATOGRAPHY; METHOXY RADICALS; METHYLENE CHLORIDE; NMR SPECTRA; TOLUENE; ULTRAVIOLET SPECTRA
- Descriptors DEC
- ALKOXY RADICALS; ALKYL RADICALS; ALKYLATED AROMATICS; ANTICOAGULANTS; AROMATICS; CARBON ISOTOPES; CARBOXYLIC ACIDS; CHROMATOGRAPHY; DRUGS; ELEMENTS; ESTERS; EVEN-ODD NUCLEI; HEMATOLOGIC AGENTS; HETEROCYCLIC COMPOUNDS; HETEROCYCLIC OXYGEN COMPOUNDS; HYDROCARBONS; HYDROGEN ISOTOPES; ISOTOPES; LACTONES; LIGHT NUCLEI; MONOCARBOXYLIC ACIDS; NUCLEI; ODD-EVEN NUCLEI; ORGANIC ACIDS; ORGANIC CHLORINE COMPOUNDS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; PYRANS; RADICALS; SEMIMETALS; SEPARATION PROCESSES; SPECTRA; STABLE ISOTOPES
Optional Information
- Notes
- 17 refs., 1 fig., 2 schemes