Extending pummerer reaction chemistry: Studies in the palau'amine synthesis area

Exploratory oxidative cyclization studies on cyclopentanelated and cyclohexenelated oroidin derivatives utilized Pummerer chemistry to generate pentacyclic structures related to the palau'amine family of sponge metabolites. Stereochemical issues were paramount, and appropriate choice of annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity for all of the core bonds.