Ga. Kraus et N. Selvakumar, Synthetic routes to pyrroloiminoquinone alkaloids. A direct synthesis of makaluvamine C, J ORG CHEM, 63(26), 1998, pp. 9846-9849
Makaluvamine 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 arom
atic substitution mediated by potassium tert-butoxide, the selective reduct
ion of a dinitro ester using catalytic hydrogenation, and the novel use of
Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthe
sis of makaluvamine C has been achieved from p-anisidine in 13.1% overall y
ield.