Bioactive dehydro--viniferin was synthesized through an efficient and practical eight-step route, achieving an overall yield of 27%. The synthesis process involves an intramolecular cyclization and dehalogenation a metal-halogen exchange, producing 3-arylbenzofuran, with the di-iodinated -aryloxyketone serving as the key intermediate. Long reaction times and the use of excess reagent -PrMgCl·LiCl facilitate metal-halogen exchange cyclization and dehalogenation. This synthetic approach, scalable for the production of analogs, was successfully conducted for the first time in multigram quantities.
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