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Modular terpene synthesis enabled by mild electrochemical couplings.

ABSTRACT: The synthesis of terpenes is a large field of research that is woven deeply into the history of chemistry. Terpene biosynthesis is a case study of how the logic of a modular design can lead to diverse structures with unparalleled efficiency. This work leverages modern nickel-catalyzed electrochemical sp²-sp³ decarboxylative coupling reactions, enabled by silver nanoparticle-modified electrodes, to intuitively assemble terpene natural products and complex polyenes by using simple modular building blocks. The step change in efficiency of this approach is exemplified through the scalable preparation of 13 complex terpenes, which minimized protecting group manipulations, functional group interconversions, and redox fluctuations. The mechanistic aspects of the essential functionalized electrodes are studied in depth through a variety of spectroscopic and analytical techniques.

SUBMITTER: Harwood SJ

PROVIDER: S-EPMC9248352 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Modular terpene synthesis enabled by mild electrochemical couplings.

Harwood Stephen J SJ Palkowitz Maximilian D MD Gannett Cara N CN Perez Paulo P Yao Zhen Z Sun Lijie L Abruña Héctor D HD Anderson Scott L SL Baran Phil S PS

Science (New York, N.Y.) 20220217 6582

The synthesis of terpenes is a large field of research that is woven deeply into the history of chemistry. Terpene biosynthesis is a case study of how the logic of a modular design can lead to diverse structures with unparalleled efficiency. This work leverages modern nickel-catalyzed electrochemical sp<sup>2</sup>-sp<sup>3</sup> decarboxylative coupling reactions, enabled by silver nanoparticle-modified electrodes, to intuitively assemble terpene natural products and complex polyenes by using s ...[more]

PMID: 35175791

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