The natural product VM55599 is a structurally complex polycyclic indole alkaloid bearing a highly substituted pyrrolidine ring. Alkaloids within this family of natural products display insecticidal, antihelmintic and antinematodal activity, and efficient synthetic routes to these alkaloids could prove useful in the development of new drug leads. New synthetic methodologies that rapidly assemble highly functionalized pyrrolidine systems as precursors to such complex targets in a stereocontrolled fashion are highly desirable. Toward these goals, our lab has recently developed a novel one-pot, multicomponent protocol for assembling pyrrolidine rings via a high yielding, endo-selective, domino 2-aza-Cope-[3+2] dipolar cycloaddition. Investigations of this work have led to the synthesis of a series of complex heterocyclic scaffolds. Further elaboration of the resultant pyrrolidine ring via a Pauson-Khand cycloaddition and subsequent ring expansion of model substrates are currently under investigation as a new approach toward VM55599 and related natural products.

Applications of a 2-aza-Cope/1,3-dipolar cycloaddition toward the synthesis of complex heterocycles

244th National Meeting (2012)

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