Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers

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  • Kubota Mio
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Saito Tatsuo
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Miyamoto Kazunori
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Hirano Keiichi
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Wang Chao
    Graduate School of Pharmaceutical Sciences, The University of Tokyo Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory, RIKEN
  • Uchiyama Masanobu
    Graduate School of Pharmaceutical Sciences, The University of Tokyo Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory, RIKEN

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Abstract

We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.

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