Modular terpene synthesis enabled by mild electrochemical couplings

Science. 2022 Feb 18;375(6582):745-752. doi: 10.1126/science.abn1395. Epub 2022 Feb 17.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Cyclization
  • Electrochemical Techniques
  • Electrodes
  • Metal Nanoparticles
  • Nickel / chemistry
  • Oxidation-Reduction
  • Silver
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Biological Products
  • Terpenes
  • Silver
  • Nickel