Nitrogen containing htereocycles are of unparalleled importance in natural product, bioorganic and medicinal chemistry. The presence of pyridine/piperidine ring systems in bioactive materials of pharmaceutical significance mandates the need of synthetic methods for accessing substituted analogues. We are interested in developing novel synthetic strategies using simple pyridine derivatives as precursors to more complex structural motifs through application of intramolecular annulation strategies. We recently discovered a gold catalyzed annulation involving an alkynone positioned for 5 or 6 endo dig cyclization upon anhydro base generation. Processing of the so formed cycloadducts under hydrolytic conditions then affords the substituted pyridine.

Metal catalyzed intramolecular additions to alkynones via anhydrobase intermediates

245th National Meeting (2013)

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