Terpenes are molecules derived from a central molecule called isoprene. These isoprene-based molecules react with each other to form larger molecules of terpenes. These molecules have been of a big interest in pharmaceutical research. The problem with some of the research is that most terpenes are highly volatile which makes synthesis difficult in environments that aren’t stable or controlled well. With this, we explore into the synthesis of our novel sesquiterpenoid molecule derived from a cadinane terpene backbone. With this synthesis, we synthesize our molecule from the structure of carvone and purify their enantiomers using flash chromatography. With this we use the design of experiments technique to optimize our reaction. This technique involves using a controlled environment, for us NMR tubes in an aluminum heating block, which allows us to manipulate temperature, concentration or any other variable to receive results that allow us to better optimize the reaction. This optimization often improves purity and yield. With this, we will proceed with our reaction using flow chemistry. Flow chemistry allows for better control of our reaction which is imperative for volatile compounds and highly reactive reagents. From this the stereochemistry is studied. More molecules could be derived, five to ten, in the future from our novel cadinane sesquiterpenoid.

Design and synthesis of a novel sesquiterpenoid from a cadinane backbone

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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