Issue 49, 2019

Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

Abstract

Bicyclic ether scaffolds are found in a variety of natural products and are of interest in probe and drug discovery. A palladium-catalyzed cascade reaction has been developed to provide efficient access to these scaffolds from readily available linear diene–diol substrates. A Pd redox-relay process is used strategically to transmit reactivity between an initial oxypalladative cyclization and a subsequent π-allyl-Pd cyclization at remote sites. The reaction affords a variety of bicyclic ether scaffolds with complete diastereoselectivity for cis-ring fusion.

Graphical abstract: Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

Supplementary files

Article information

Article type
Communication
Submitted
16 May 2019
Accepted
17 May 2019
First published
31 May 2019

Chem. Commun., 2019,55, 7013-7016

Author version available

Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

M. C. Lux, M. L. Boby, J. L. Brooks and D. S. Tan, Chem. Commun., 2019, 55, 7013 DOI: 10.1039/C9CC03775F

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