Kimber, Marc CAnderberg, Pia IHarding, Margaret2015-12-130040-4020http://hdl.handle.net/1885/73506ABC analogues of the antitumour antibiotic streptonigrin, that contain the key metal chelation site and redox-active quinone unit that are essential for biological activity, were prepared via palladium catalysed cross-coupling of 2-iodo-8-nitroquinoline or 2-iodo-6-methoxy-5-nitroquinoline with 2- trimethylstannio-6-methylpyridine. Mild oxidation of the pyridyl methyl group introduced the acid functional group on ring C and Fremy's salt oxidation afforded the quinone unit which was elaborated to give the 5-amino-6-methoxy substitution pattern present in streptonigrin. 2000 Elsevier Science Ltd.Keywords: antineoplastic antibiotic; palladium complex; rufocromomycin; rufocromomycin derivative; unclassified drug; article; catalyst; drug structure; drug synthesis; oxidation; priority journal; structure activity relation; structure analysis Antitumour compounds; Bicyclic heterocyclic compounds; Coupling reactions; Quinolinones20002015-12-11