Patent ID: 7838677

Claim:
A process for the preparation of a nordihydrothebainone product comprising nordihydrothebainone or an analog thereof having the structure of formula 10: wherein X is selected from the group consisting of oxygen, sulfur, —S(O)—, —S(O 2 )—, —C(R 18 R 19 )—, —N(R 17 )— and —N + (R 17a R 17b )—; R 1 , R 2 , R 3 , R 4 , R 18 , and R 19 are independently selected from the group consisting of hydrogen, substituted and unsubstituted acyl, alkenyl, alkoxy, alkoxyaryl, alkyl, alkylamino, alkylthio, alkynyl, amino, aryl, arylalkoxy, carboalkoxy, carboxyalkenyl, carboxyalkyl, carboxyl, cyano, cyanoalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylether, halo, haloalkoxy, haloalkyl, heteroaryl, heterocyclic, hydroxyalkyl, hydroxyl, and nitro, or R 18 and R 19 together form keto; R 17 is selected from the group consisting of hydrogen, acyl, alkenyl, alkoxyaryl, alkyl, alkynyl, aryl, carboxyalkenyl, carboxyalkyl, cyanoalkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heteroaryl, heterocyclic, carboxyl, carboxyamide, carboxyester, hydroxyl and hydroxyalkyl; and R 17a and R 17b are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, aryl and benzyl or together form oxo; the process comprising: forming a reaction mixture comprising a β,γ-bicyclic ketone compound, a cyclizing acid and an acid anhydride to produce the nordihydrothebainone product, the β,γ-bicyclic ketone compound having the structure of formula 11: wherein X, R 1 , R 2 , R 3 , R 4 , R 17 , R 18 and R 19 and are as defined above.