A major challenge in synthetic organic chemistry is developing concise approaches to biologically active, heterocyclic natural products. Toward that end, new methods and strategies that enable the rapid assembly of the diverse heterocyclic frameworks found in such compounds are especially attractive. Retrosynthetic analysis of individual natural products can be advantageously directed in such a manner that deficiencies in available methodology can be discovered and solutions invented. Natural products are thus targets of opportunity that inspire and empower the invention and discovery of new chemistry that frequently becomes general in organic synthesis. In this context, we are developing new applications and variations of cycloadditions, electrocyclic ring-openings/cyclizations, rearrangements, Mannich and related reactions, multicomponent processes, transition metal-catalyzed transformations, and enantioselective halolactonizations as key constructions to fabricate heterocyclic subunits commonly found in natural products. Selected applications of these and other reactions to the total syntheses of selected heterocyclic natural products will be presented.

Some recent advances in the synthesis of heterocyclic natural products

245th National Meeting (2013)

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