Synthesis of the myrmicarin family of natural products

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DESCRIPTION (provided by applicant): Despite the unique and impressive complexity of the higher-order members of the myrmicarin family of natural products and their established potential to serve as valuable leads for the study of chemical biology, these secondary metabolites have remained unanswered synthetic challenges for nearly a decade. The absence of a cohesive biosynthetic pathway accounting for their formation could potentially explain this state of affairs. In this proposal, a unifying biogenetic hypothesis is advanced which outlines a clear method to accomplish the synthesis of all these compounds from two key starting materials, one of which is a simpler member of the myrmicarin family. Carefully considered synthetic pathways to the proposed materials for this sequence, facilitated by a series of designed cascade reactions and new synthetic methodologies, will enable its evaluation. The overall significance of this work resides in its promise to establish presently missing biosynthetic links for the myrmicarin family, to provide both natural and designed molecules that can serve as tools for the study of chemical biology, and to contribute generally to the advancement of synthetic organic chemistry.