We are reportiing a Diversity Oriented Synthesis using furan epoxide 1. We explored the chemistry of two reactive moieties in compound 1, the furan ring and the epoxide. We have accomplished the Achmatowicz reaction with the furan ring and the ring opening reaction of the epoxide with amines. However, our research finds that these two reactions do not happen in sequence. The product of the Achmatowicz reaction (3) does not react cleanly with amines and the product of the ring opening (3) does not react cleanly in the Achmatowicz reaction. Since related compounds of epoxide ring opening with amines have been found in a variety of bioactive molecules, our research is also testing bioactivity of our products with the Brine Shrimp Lethality Assay and a variety of cancer cell assays.

Diversity oriented synthesis for drug discovery using a furan epoxide

ACS Spring 2022

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