Synthesis of Functionalized Cyclic Ethers via Gold‐Catalyzed Cyclization and Rearrangement

Cyclic ethers are prevalent structural motifs in natural products and pharmaceuticals, and their efficient synthesis has attracted significant attention in organic synthesis. A synthetic approach for the functionalization of cyclic ethers from ortho ‐alkynylarylmethanol derivatives protected by cyclic ethers via gold‐catalyzed intramolecular cyclization and rearrangement is developed. The gold‐catalyzed 6‐ endo ‐dig cyclization yielded various functionalized cyclic ethers. Furthermore, this transformation enabled the synthesis of C ‐glycoside derivatives from alkynyl compounds bearing O ‐glycosides.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-09-23
DOI
https://doi.org/10.1002/adsc.70012
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00
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article

Synthesis of Functionalized Cyclic Ethers via Gold‐Catalyzed Cyclization and Rearrangement

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Advanced Synthesis & Catalysis
Catalytic Alkyne Reactions
article

Synthesis of Functionalized Cyclic Ethers via Gold‐Catalyzed Cyclization and Rearrangement

Hironao Sajiki, Takashi Ikawa, Kwihwan Kobayashi, Tsuyoshi Yamada, Akiko Fujii, Tomoki Hyodo
article en

Abstract

Cyclic ethers are prevalent structural motifs in natural products and pharmaceuticals, and their efficient synthesis has attracted significant attention in organic synthesis. A synthetic approach for the functionalization of cyclic ethers from ortho ‐alkynylarylmethanol derivatives protected by cyclic ethers via gold‐catalyzed intramolecular cyclization and rearrangement is developed. The gold‐catalyzed 6‐ endo ‐dig cyclization yielded various functionalized cyclic ethers. Furthermore, this transformation enabled the synthesis of C ‐glycoside derivatives from alkynyl compounds bearing O ‐glycosides.

Advanced Synthesis & Catalysis
Gifu Pharmaceutical University (JP), Aichi Institute of Technology (JP), University of Toyama (JP), National Institute of Advanced Industrial Science and Technology (JP)
Openalex Percentile: Top 80%
Catalytic Alkyne Reactions
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