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A novel approach to the pyridoacridine ring system of the ascididemin-type marine alkaloids is presented. This approach allows for the introduction of the ring A of the alkaloids by using a simple aromatic aldehyde building block. The viability of this approach is demonstrated with the synthesis of AK37, a bioactive deaza analogue of the alkaloid ascididemin. Starting from 3-cyano-4-methylquinoline, a sequence of regioselective homolytic benzoylation, annulation of a bromopyridine ring, and radical cyclization leads to the pentacyclic ring system.

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A Novel Approach to the Pyridoacridine Ring System: Synthesis of the Topoisomerase Inhibitor 13-Deazaascididemin. -A novel approach to the pyridoacridine ring system of ascididemin-type marine alkaloids is development and applied to the synthesis of the bioactive deaza analogue of ascididemin AK37 (VII). -(RAEDER, S.; BRACHER*, F.; Arch. Pharm. (Weinheim, Ger.) 345 (2012) 10, 822-826, http://dx.