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Open Access Publications from the University of California

Progress Towards a Formal Enantiospecific Total Synthesis of Potent Antimalarial (-)-7-Isocyano-11(20),14-epiamphilectadiene and Preliminary Investigations of Carbene [2,3]-Wittig Reactions and Epoxypolyene Polycyclizations

  • Author(s): Freidberg, Michael
  • Advisor(s): Vanderwal, Chris
  • et al.
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Total synthesis and methodology are two large fields of study in synthetic organic chemistry which serve to expand available reactions and strategies with the overarching goal of revealing unique and concise solutions to complex chemical problems. Achievements in these fields are crucial for current and future reasonable syntheses of bioactive compounds of interest in order to evaluate potentially useful materials. Our efforts to contribute to these endeavors included the attempted formal synthesis of an antimalarial isocyanoterpene (ICT) and the investigation into the expansion of the carbene [2,3]-Wittig and polycyclization methodologies.

Malaria currently causes millions of infections yearly, and the drugs that are commonly used to treat it are losing efficacy. ICTs are a class of compounds that show great potential for becoming the basis of a new class of antimalarials that are believed to act via traditional and non-traditional routes to eliminate the malaria parasite. To improve upon the synthesis of one of the most potent ICTs, reported by Shenvi, we chose to pursue an enantiospecific formal synthesis of (-)-7-Isocyano-11(20),14-epiamphilectadiene.

In the course of our investigations into two separate methodologies, we gained insight into the [2,3]-Wittig rearrangement of various carbenes and the polycyclization of 2,2-disubstituted epoxides and established reliable routes to substrates for the latter. It is our hope that this progress—in addition to future contributions from our lab—aids in the development of expedient and concise syntheses of useful bioactive compounds.

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This item is under embargo until February 5, 2020.