Dihydronorthevinone (2b) was prepared from dihydrothevinone (2a) with
diethyl azodicarboxylate (DEAD) and transformed into a number of new N
-substituted dihydronorthevinone derivatives (2c-2g). Grignard reactio
ns of the new compounds with methylmagnesium iodide and tert-butyl-mag
nesium chloride were studied. O-Demethylation of 3a-3j resulted in the
corresponding N-substituted buprenorphine and diprenorphine analogs 4
a-4j.