The synthesis of the Lycopodium alkaloid cermizine D was accomplished after extensive optimization using a dihydropyridone-based functionalization strategy. The synthesis is concise using six steps from 4-methoxypyridine with a 13% overall yield. Central in this synthesis was a diastereoselective copper-mediated 1,4-addition of a cuprate derived from 2-((trimethylsilyl)methyl)pyridine to a bicyclic 2,3-dihydropyridone. A Wittig olefination followed by two consecutive hydrogenations provided the natural product.

Six-step synthesis of cermizine D

246th National Meeting (2013)

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