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4,5-Diaryl-1 H -pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: synthesis and evaluation as anti-mitotic and cytotoxic agents

Banwell, Martin; Hamel, Ernest; Hockless, David; Verdier-Pinard, Pascal; Willis, Anthony; Wong, David


The 4,5-diarylated-1H-pyrrole-2-carboxylates 3-8 have each been prepared as hybrids of the potent anti-mitotic agent combretastatin A-4 (1) and the similarly active marine alkaloid lamellarin T (2). The key steps involved selective lithium-for-halogen exchange at C5 within the N-PMB protected 4,5-dibromopyrrole 22 and Negishi cross-coupling of the derived zincated species with the relevant aryl iodide. The ensuing 5-aryl-4-bromopyrrole then engaged in Suzuki-Miyaura cross-coupling with the...[Show more]

CollectionsANU Research Publications
Date published: 2006
Type: Journal article
Source: Bioorganic and Medicinal Chemistry
DOI: 10.1016/j.bmc.2006.02.018


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