The specific goal of this research proposal is the total synthesis of the indoline alkaloid communesin B.Communesin B is a broadly biologically active natural product that posseses two vicinal quaternary centersand two aminal moeities embedded within a heptacyclic framework. There have been no reported totalsyntheses to date. The successful synthesis of this compound would represent an important advance in thefield of alkaloid synthesis. The key step in the synthesis of communesin B would be a Mo-, Ir-, or W-catalyzed asymmetric allylic alkylation (AAA) reaction which will employ indole derivatives as thenucleophile. The use of indoles nucleophiles in the AAA reaction has not been precedented and would be asignificant extension of the current AAA technology.
