Efficient total synthesis of dehydro-δ-viniferin through metal-halogen exchange cyclization

被引：0

作者：

Cao, Jinfang ^{[1
]}

Zhu, Qibin ^{[1
]}

Sha, Zhen ^{[1
]}

Zhou, Xiaoxuan ^{[1
]}

Zhu, Ruitong ^{[1
]}

Yao, Chunsuo ^{[1
]}

机构：

[1] Chinese Acad Med Sci & Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Inst Mat Med, Beijing 100050, Peoples R China

来源：

RSC ADVANCES | 2025年 / 15卷 / 10期

关键词：

Chlorination - Lithium Chloride - Reaction intermediates - Synthesis (chemical);

D O I：

10.1039/d5ra00960j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bioactive dehydro-delta-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 alpha-aryloxyketone serving as the key intermediate. Long reaction times and the use of excess reagent i-PrMgCl<middle dot>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.

引用

页码：7738 / 7741

页数：4

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