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Updated: Jun 7, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Biomimetic Radical Oligomerization Enables the Total Synthesis of Five Resveratrol Dimers
Travis A Hammerstad1, Bec J Roldan1, Kyle Schoenmakers2
1Department of Chemistry, University of Michigan, Ann Arbor, 930 N University Ave, Ann Arbor, Michigan 48109, United States.
Abstract:
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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