title: Total synthesis of cytotoxic metabolite ( ± )-desmethyldiaportinol from Ampelomyces sp.
abstract: A concise total synthesis of ( ± )-desmethyldiaportinol isolated from Ampelomyces sp. is described. Microwave-assisted cyclocondensation of 3,5-dimethoxyhomopthalic acid with 3,4-dibromobutanoyl chloride afforded the 3-(2,3-dibromopropyl)-6, 8-dimethoxyisocoumarin in 2-3 min as the pivotal step. The 3,4-dibromobutanoyl chloride was itself synthesised from 3-butenoic acid via bromination in carbon tetrachloride at room temperature to yield 3,4-dibromobutanoic acid followed by reaction with thionyl chloride. The replacement of bromo- by hydroxyl substituent was achieved under mild conditions involving the refluxing in a mixture of acetone and water to provide ( ± )-3-(2,3-dihydroxypropyl)-6,8-dimethoxyisocoumarin which on complete demethylation furnished the title natural product.
authors.affiliation: a Department of Chemistry , Quaid-I-Azam University , 45320 Islamabad , Pakistan.
authors.forename: Aamer
authors.initials: A
authors.lastname: Saeed
authors.forename: Muhammad
authors.initials: M
authors.lastname: Qasim
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D002251:Carbon Tetrachloride / Q000494:pharmacology; D049934:Isocoumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D049934:Isocoumarins; C000591039:desmethyldiaportinol; D002251:Carbon Tetrachloride