This application describes the development of sequential cycloadditions for the stereocontrolled synthesis of indole alkaloids framework and its application toward the synthesis of a new indole alkaloid--3-demethoxymyrtoidine. The proposed methodology seeks to explore a reaction sequence of a two-components system to realize tandem [4 + 2] / [3 + 2] cycloadditions. The sequence will be carried out in an intra-intermolecular fashion, or in a reversed, inter-intramolecular fashion. A three-component intermolecular tandem reaction will also be implemented, and will make use of chiral dienophile to obtain selectivity in the cycloadditions. We also intend to apply this methodology to build the core structure of 11-demethoxymyrtoidine, a new chloroquine adjuvant alkaloid, important in the treatment of malaria.
