TY - JOUR AU - Machara, Aleš; Endoma-Arias, Mary Ann A.; Císařova, Ivana; Cox, D. Phillip; Hudlický, Tomáš TI - Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine SN - 0039-7881 SN - 1437-210X PY - 2016 JO - Synthesis JF - Synthesis LA - EN VL - 48 IS - 12 SP - 1803 EP - 1813 ET - 2016/04/19 DA - 2016/06/02 KW - alkaloids KW - iron–diene complexes KW - nororipavine synthesis KW - iron decomplexation KW - demethylation AB - Thebaine was converted into its iron tricarbonyl complex, which underwent successive N- and O-demethylation with BrCN and BBr3, respectively. Decomplexation of the iron tricarbonyl moiety was accomplished with ammonium cerium(IV) nitrate (CAN) and base-catalyzed hydrolysis furnished nororipavine. When excess CAN was used the methoxydiene unit was converted into its C-14 nitrate that on hydrogenation and further hydrolysis furnished noroxymorphone. Full experimental and spectral data are provided for all key compounds. PB - © Georg Thieme Verlag DO - 10.1055/s-0035-1561435 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0035-1561435 ER -