Recently, guanacastepene A, found growing on the branches of the Daphnopsis americana tree in Costa Rica, has been of specific synthetic interest. Guanacastepene A shows great promise for the treatment of vancomycin resistant Staphylococcus aureus and methicillin resistant Enterococcus faecalis due to the inherent antibiotic activity of the compound. Our synthetic approach toward the guanacastepene A-B-C ring system is based on previous work done in our laboratories, which involves a [3,3] sigmatropic Claisen rearrangement to generate a variety of polycyclic ring structures. Thus, it was reasoned that this strategy could be employed to assemble the requisite bicyclo[5.3.0]decane A-B ring core of guanacastepene A. To decrease the reaction time and increase the efficiency of the reaction, the Ovaska group found that microwave irridation (MWI) optimized the reaction by shortening reaction times and increasing the yields significantly. Thus far the desired A-B ring system has been produced in good yield. Future efforts will focus on completion of the tricyclic guanacastepene ring core and introduction of the remaining functional groups.

Synthetic strategies towards the synthesis of guanacastepene A

253rd National Meeting (2017)

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