Bioactive polycyclic compounds are derived from both natural sources and from purely synthetic approaches. Non-natural polycyclic small molecules with novel scaffolds are sought after as potential leads in the drug discovery process. The development of new cyclization strategies for rapid assembly of complex building blocks for small molecule synthesis will be described. These strategies have arisen from our work on the stereospecific Nazarov electrocyclization, a multistep cationic process that most commonly affords cyclopentenone products. Depending upon how the Nazarov pentadienyl and cyclic allyl cationic intermediates 1 and 2 are designed, different reaction pathways can be favored and disfavored, enabling the stereocontrolled synthesis of a variety of different cyclopentanoid derivatives. A new method for generating intermediates of type 1 from readily available reactants, obviating the use of the typical divinyl ketone precursor, will also be presented.

Reaction cascades for building complex carbocycles and heterocycles from simple precursors

255th National Meeting (2018)

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