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Total synthesis of marinoquinoline A using a palladium(0)-catalyzed Ullmann cross-coupling reaction

Ma, Xinghua; VO, Yen Thi-Hoang; Banwell, Martin; Willis, Anthony


The title natural product, 1, has been synthesized. The pivotal steps are a Pd0-catalyzed Ullmann cross-coupling of the 3-iodopyrrole-2-carboxaldehyde 13 with o-bromonitrobenzene (14), conversion of the resulting 3-arylpyrrole 15 into methylketone 17, and reductive cyclization of 17 by using magnesium in methanol to give target 1 in 85% yield. Coming together: A convergent synthesis of the biologically active alkaloid marinoquinolineA, which embodies a 3H-pyrrolo[2,3-c]quinolone ring system,...[Show more]

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
Source: Asian Journal of Organic Chemistry
DOI: 10.1002/ajoc.201200037


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