About the Chemistry

 The molecule of interest in this paper is the manzamine alkaloid (–)-nakadomarin A which has been isolated from the marine sponge Amphimedon. This molecule demonstrates many biological activities, mainly being cytotoxic activity that basically serves as a carcinopreventive agent and an antimicrobial. This includes activity against murine lymphoma L1210 cells, inhibition of cyclin-dependent kinase 4 which is associated with tumorigenesis of a variety of cancers, and antimicrobial activity against the Gram-positive bacterium Corynebacterium xerosis and the fungus Trichophyton mentagrophytes. Molecule 10, the molecule of interest to us, is one of the beginning reagents of the synthesis of (–)-nakadomarin A. Molecule 8 is used to synthesize Molecule 10.

Reaction Scheme