Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin

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dc.contributor.authorSang Hee Kim-
dc.contributor.authorGao Jun Fan-
dc.contributor.authorJae Kwang Lee-
dc.contributor.authorJung Joon Lee-
dc.contributor.authorDeuk Joon Kim-
dc.date.accessioned2017-04-19T08:59:02Z-
dc.date.available2017-04-19T08:59:02Z-
dc.date.issued2002-
dc.identifier.issn0022-3263-
dc.identifier.uri10.1021/jo010789bko
dc.identifier.urihttps://oak.kribb.re.kr/handle/201005/5831-
dc.description.abstractA practical synthetic route to 4-acetylisocoumarins and the first total synthesis of AGI-7 (5) and sescandelin (4) are described. The readily available homophthalate 8 was transformed to the vinylogous amide ester 13 in high overall yield. Upon treatment of 13 with refluxing aqueous formic acid, the desired 4-acetylisocoumarin (5) and its regioisomer 3-methyl-4-formylisocoumarin (17) were produced in a 3:1 ratio. After separation of the desired product (5) from the unwanted minor isomer, the enantioselective reduction of AGI-7 by borane in the presence of Corey's (S)-oxazaborolidine reagent afforded (+)-sescandelin (4) with a 93% ee.-
dc.publisherAmer Chem Soc-
dc.titleSynthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin-
dc.title.alternativeSynthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin-
dc.typeArticle-
dc.citation.titleJournal of Organic Chemistry-
dc.citation.number9-
dc.citation.endPage3130-
dc.citation.startPage3127-
dc.citation.volume67-
dc.contributor.affiliatedAuthorJung Joon Lee-
dc.contributor.alternativeName김상희-
dc.contributor.alternativeName판가준-
dc.contributor.alternativeName이재광-
dc.contributor.alternativeName이정준-
dc.contributor.alternativeName김덕준-
dc.identifier.bibliographicCitationJournal of Organic Chemistry, vol. 67, no. 9, pp. 3127-3130-
dc.identifier.doi10.1021/jo010789b-
dc.description.journalClassY-
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