Artemone is an antifungal natural product found in the Indian sage <i>Artemisia pallens</i>. By mimicking the plant's presumed biosynthetic route, we have completed a protecting-group-free, four-step synthesis of (+)-artemone from (-)-linalool, featuring a stereoselective organocatalytic conjugate addition,γ-prenylation, and oxidation of a sterically congested alcohol. The intramolecular conjugate addition step is particularly noteworthy, as it combines a weak nucleophile with an α-substituted enal. This synthesis rapidly generates 3 stereocenters, is conducted entirely at room temperature, and minimizes redox manipulations.

Organocatalytic and protecting-group-free synthesis of (+)-artemone

249th National Meeting (2015)

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