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Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-?-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 ?-allyl-Pd cyclization at remote sites. The reaction affords a variety of bicyclic ether scaffolds with complete diastereoselectivity for cis-ring fusion.

SUBMITTER: Lux MC

PROVIDER: S-EPMC6601619 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Lux Michaelyn C MC Boby Melissa L ML Brooks Joshua L JL Tan Derek S DS

Chemical communications (Cambridge, England) 20190531 49

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 sca ...[more]

PMID: 31147660

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