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Demonstrates effective synthesis of resveratrol dimers, suggesting useful pathways for complex compound development.
A biomimetic platform for the selective synthesis of dihydrobenzofuran (DHB)-containing resveratrol dimers from differentiated resveratrol monomers is disclosed. Controlled radical coupling directed by the persistent radical effect enables access to the C3-, C10-, and C12-linked DHB manifolds, providing concise syntheses of δ-viniferin, ε-viniferin, and gnetin C. Divergence from the C10-DHB series also enables the synthesis of ampelopsin B and ampelopsin F. Experimental selectivity trends, supported by DFT calculations, are consistent with regioselectivity arising from radical localization within transient resorcinol intermediates.
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Hammerstad et al. (2026) studied this question.
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