Researchers from University of Basel developed a synthesis method for terpene that is inspired from natural process.
Terpenes are organic compounds that are produced by variety of plants and some insects. Terpenes are the primary constituents of several essential oils, steroids, and clinically relevant substances. They are however, difficult to synthesize in the laboratory. Several refined methods to artificially synthesize terpene that are structurally complex compounds require numerous synthesis steps with low yields. Now researchers from University of Basel developed a synthesis method for terpene that is inspired from natural process. The research led by Professor Konrad Tiefenbacher from the University of Basel’s Department of Chemistry, includes a decisive step that takes place in the cavity of a molecular capsule— resorcinarene. Although, the capsule has been known for around 20 years, its catalytic effect has only very recently been described. The capsule forms itself from six smaller compounds that are ring-shaped in organic solvents with the help of hydrogen bonds.
Inspired from the natural process, the researchers began with a starting material for the synthesis. The material is enclosed by the capsule that enables the formation of the terpene. Moreover, unwanted side effects in the process are restricted by control elements previously integrated into the precursor. These elements further direct the transformation towards the desired product. The researchers conducted four-step synthesis of the natural product—isolongifolene to prove the applicability of the concept. Isolongifolene with the formation of a ring-shaped terpene compound was catalyzed by the capsule in significantly fewer steps and with a good yield. The reaction mechanism was clarified by using labeled precursors and computer simulations. The researchers aim to use capsules as an artificial enzyme in manufacturing of complex terpenes, either by modifying the existing system or by developing new catalysts. The research was published in the journal Nature Catalysis on July 30, 2018.