Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
Pages 54-55
Veiutamine, a new type of marine indroiminoquinone alkaloid, was isolated from the Fijian sponge Zyzzya fuliginosa by Ireland group in 1997. Veiutamine exhibits a potential antitumor activity (IC50 0.3μg/ml).We are currently developing the synthesis of bioactive condensed heterocyclic compounds based on the electrocyclic reaction of either 6π-electron system or aza 6π-electron system incorporating the aromatic one double bond. We planned the total synthesis of veiutamine by an application of this methodology. In the present work, we here describe the synthesis of deoxyveiutamine through the construction of the poly-functional indole framework based on a thermal electrocyclic reaction of 3-allenyl-2-alkenylpyrrole intermediate derived from 3-propargylpyrrole. The indole was converted into indolequinone in several steps. A conversion of indolequinone to deoxyveiutamine are now in progress.
