Guaipyridine alkaloids are a rare family of natural products characterized by a pyridine-fused cycloheptane structure. Examples include cananodine, isolated from <i>Cananga odorata</i>, and the rupestines, isolated from <i>Artemesia rupestris</i>. We have previously explored the creation of the pyridine-fused cycloheptane core using an intramolecular epoxide opening. Here we present our results using an intramolecular Heck coupling approach to the seven-membered ring of the guaipyridine targets.

Synthetic studies on guaipyridine alkaloids: Intramolecular Heck approach

249th National Meeting (2015)

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