The tetrahydrothebaine ester (1) has been converted by the Curtius reaction into 7α-amino-6,14-endo-etheno-tetrahydrothebaine (3; R = H) and its 6,14-ethano-analogue. The amine and its 1-chloro-derivative have also been prepared from the ketone (6) by the Schmidt reaction. The amine has been rearranged to the benzazocine (4) by methylation and Hofmann degradation, and its 1-chloro-derivative has been rearranged by nitrous acid to the ketone (8).