Synthesis of the Dimeric Diarylheptanoids Alpinidinoid C and Officinine B Enabled by Blue-Light-Mediated Triple-Minisci-Type Alkylation.

The first syntheses of the natural products alpinidinoid C and officinine B are reported. These unusual dimeric diarylheptanoids were accessed from a 3-substituted pyridine intermediate via a blue-light-mediated, triple-Minisci-type alkylation. Very few reports utilize -(acyloxy)phthalimides (NAPs) in the construction of natural products, and the syntheses reported herein highlight the power of this methodology toward the orthogonal construction of highly substituted arenes.