New synthetic methodologies have been developed which permit the regioselective hydroamination of propargylguanidines in either a 5-exo-dig or 6-endo-dig fashion. This transformation gives rise to five or six membered ring guanidine containing heterocyclic cores. The use of this methodology in the synthesis of polycyclic guanidinium ion containing natural products, e.g. saxitoxin and naamidine A, will be highlighted. Extensions of this methodology to other important heterocyclic scaffolds such as dihydropyrimidones will also be discussed.

Propargylguanidine hydroaminations and their application to important hetereocyclic systems

244th National Meeting (2012)

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