The guaipyridine alkaloids are a small family of natural products comprised of the eponymous compound, cananodine and the rupestines. The rupestines were isolated from <i>Artemisia rupestris</i>, a plant common in traditional Chinese folk medicine, but no biological activity has yet been reported for these compounds. Our synthetic approach to the guaipyridine skeleton involves an alkylation of a picolyl bromide derivative followed by an intramolecular Heck reaction to form the seven-membered carbocycle of the targets.  Progress on the synthesis of rupestines B-D and G will be reported.

Synthetic studies on guaipyridine alkaloids: Rupestines B-D and G

253rd National Meeting (2017)

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