2024
DOI: 10.1021/acs.orglett.4c03227
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Synthesis of the Dimeric Diarylheptanoids Alpinidinoid C and Officinine B Enabled by Blue-Light-Mediated Triple-Minisci-Type Alkylation

Daniel C. Schultz,
Upendra Rathnayake,
Renn A. Duncan
et al.

Abstract: The first syntheses of the Alpinia officinarum 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 N-(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.

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