期刊
NATURAL PRODUCT RESEARCH
卷 28, 期 3, 页码 185-190出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2013.866111
关键词
desmethyldiaportinol; isocoumarin; Ampelomyces sp
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 2-3min 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.
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