Exploring symmetry-based logic for a synthesis of palau'amine.

ABSTRACT

A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms the imbedded spirocyclopentane motif observed in the natural product. A host of atypical reactions and processes developed during these studies are discussed, as are plans for completing total syntheses of this compound class.