Natural Product Synthesis (1)

The first two weeks in the lab began with setting up the lab and making necessary stock solutions and solvent systems for organic synthesis. The goal for this summer is to continue to investigate the reaction mechanisms of p-methylbenzoquinone and prenyl bromide, a novel one-step synthesis to attach the prenyl side chain onto the quinone molecule. Through extensive literature research, we have confirmed that our concise synthetic methods that have developed over the last two years are not reported in any peer-reviewed journals. In addition, we have yielded two regioisomers on para and meta positions, with meta isomer being the first-time synthetic product. Although the reaction mechanisms are still elusive at this time (and will be unexplainable in a long future), we have confirmed the identity of the molecules through rigorous analytical methods.


Building onto our past success, a new reaction with (S)-(+)-citronellyl bromide at similar reaction conditions was tried out. Unfortunately, as 99% of organic synthese do not work while you think they work, no reaction has occurred after several failed attempts. But that has provided us with valuable insights on the reaction mechanisms – stay tuned for next week!