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Divergent Synthesis of Pyrone Diterpenes via Radical Cross Coupling.

ABSTRACT: A divergent strategy for assembling pyrone diterpenes is presented. Capitalizing on the unique stereo- and chemoselectivity features of radical-based chemistry, the core decalin of these structures is efficiently forged using an electrochemically assisted oxidative radical polycyclization while key peripheral substituents are appended using decarboxylative radical cross couplings. In this way, access to four natural products (subglutinols A/B, higginsianin A, and sesquicillin A) is achieved in a concise and stereocontrolled fashion that is modular and amenable to future medicinal chemistry explorations.

SUBMITTER: Merchant RR

PROVIDER: S-EPMC6016063 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Divergent Synthesis of Pyrone Diterpenes via Radical Cross Coupling.

Merchant Rohan R RR Oberg Kevin M KM Lin Yutong Y Novak Alexander J E AJE Felding Jakob J Baran Phil S PS

Journal of the American Chemical Society 20180611 24

A divergent strategy for assembling pyrone diterpenes is presented. Capitalizing on the unique stereo- and chemoselectivity features of radical-based chemistry, the core decalin of these structures is efficiently forged using an electrochemically assisted oxidative radical polycyclization while key peripheral substituents are appended using decarboxylative radical cross couplings. In this way, access to four natural products (subglutinols A/B, higginsianin A, and sesquicillin A) is achieved in a ...[more]

PMID: 29921130

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