This project will examine the ISNC reactions of unsaturated nitrocyanoethers. The nitrocyanoether is prepared from a Michael addition with nitrostyrene. Several synthetic routes were investigated to yield a series of Michael donors: α-hydroxy esters, propargylic and allylic cyanohydrins. Crotonaldehyde was converted to the allylic cyanohydrin in good yields and utilized to optimize reaction conditions for the cyanohydration of the propargylic system. Oxidation of propargyl alcohol yielded the corresponding aldehyde which was then converted to the propargylic cyanohydrin in poor yields with difficult separations. An alternative route to the propargyl nitroether involved the Grignard reaction of ethyl glyoxalate with ethynylmagnesium bromide. The former cyanohydrins and α-hydroxy esters could be converted to nitroethers for ISNC reactions yielding 2,3-derivatized furans. Computational work in our group suggests that these furans could be incorporated into a novel tetrafuromacrolide that could function as an ionophore similar to nonactin.<br/>

Preparation of α-hydroxy esters, propargylic, and allylic cyanohydrins for ISNC reactions

251st National Meeting (2016)

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