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A Redox-Relay Heck Approach to Substituted Tetrahydrofurans.

ABSTRACT: An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans, including the calyxolane natural products.

SUBMITTER: Byrne TJM

PROVIDER: S-EPMC10088021 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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A Redox-Relay Heck Approach to Substituted Tetrahydrofurans.

Byrne Tom J M TJM Mylrea Megan E ME Cuthbertson James D JD

Organic letters 20230329 13

An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available <i>cis</i>-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans, including the calyxolane natural products. ...[more]

PMID: 36988968

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