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Synthetic route to 4,5-epoxy-ring opened 5,6-didehydromorphinan-6-carbonitriles, 5a and 6a. Starting from oxycodone (5) and 14-O-methyloxycodone (6), the expected carbonitriles were not obtained. Instead, the ether bridge between position 4 and 5 of the starting compound was opened and the respective acrylonitrile derivatives 5a and 6a were formed exclusively. Reagents and conditions: (a) TosMIC, potassium tert-butoxide (t-BuOK), dimethyl ether (DME), tert-butanol (t-BuOH), 0 °C.
