Modular terpene synthesis enabled by mild electrochemical couplings

TLDR

Terpene synthesis is a major field of research, and terpene biosynthesis demonstrates how modular design can generate diverse structures with unparalleled efficiency. The study aims to use nickel‑catalyzed electrochemical decarboxylative coupling with silver‑nanoparticle electrodes to assemble terpene natural products and complex polyenes from simple modular building blocks. The authors employ this nickel‑catalyzed electrochemical decarboxylative coupling on silver‑nanoparticle electrodes and investigate the electrode mechanism using spectroscopic and analytical methods. The method enables scalable synthesis of 13 complex terpenes with reduced protecting group manipulations, functional group interconversions, and redox fluctuations, demonstrating a step change in efficiency.

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.