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Efficient total synthesis of dehydro-δ-viniferin through metal-halogen exchange cyclization
Jinfang Cao1, Qibin Zhu1, Zhen Sha1
1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 P. R. China yaocs@imm.ac.cn.
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.
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