Efficient total synthesis of dehydro-<i>δ</i>-viniferin through metal-halogen exchange cyclization.

ABSTRACT: Bioactive dehydro-δ-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 via a metal-halogen exchange, producing 3-arylbenzofuran, with the di-iodinated α-aryloxyketone serving as the key intermediate. Long reaction times and the use of excess reagent i-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.

SUBMITTER: Cao J 

PROVIDER: S-EPMC11895512 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature