Imelda Hot
UIC
Zamamaphidin A, a novel manzamine-like alkaloid recently isolated in very small quantities from the Okinawan sponge Amphimedon sp., displays significant inhibitory properties against the human pathogen Staphylococcus aureus. The structural complexity of this polycyclic marine natural product and its biological activity, coupled with our interest in the application of heteroatom-stabilized nitrenium ions to organic synthesis, has led us to initiate a model study directed toward construction of the densely-functionalized pentacyclic core. This work has led to the development of a versatile method for the intramolecular anti amidooxysulfonylation of alkenes. Details of this nitrenium ion-mediated cyclofunctionalization together with an account of our progress toward the synthesis of the core of zamamaphidin A will be presented.