Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine CThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractMakaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassiumtert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthesis of makaluvamine C has been achieved from p-anisidine in 13.1% overall yield.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge A. Kraus and Natesan Selvakumar. "Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine C" The Journal of Organic Chemistry Vol. 63 Iss. 26 (1998) p. 9846 - 9849
Available at: http://works.bepress.com/george_kraus/114/