The prospect of synthesizing a pyrrolizidine alkaloid (a 5,5-fused bicyclic, nitrogen-containing heterocycle) utilizing an intramolecular Schmidt reaction coupled with stereocontrol through allylic azide rearrangement was studied. Conditions toward a key intermediate were altered, such as; temperature, strong acids, and solvents to name a few. The aim of this was to seek out a set of optimally efficient conditions for this strong acid promoted ring closing, with the overall goal of stereoselectively forming this key intermediate in good product ratios in order to be able to proceed with another experimental route towards a 3,5-disubstituted pyrrolizidine natural product.

Natural product application of a combined allylic azide rearrangement intramolecular Schmidt reaction

247th National Meeting (2014)

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