1574527-14-2Relevant academic research and scientific papers
Total synthesis of 8,14-dihydromorphinandienone alkaloids
Ghavimi, Bahman,Magnus, Philip
supporting information, p. 1708 - 1711 (2014/04/17)
A collective synthesis of 8,14-dihydronorsalutaridine, 8,14- dihydrosalutaridine, norisosinomenine, and isosinomenine is reported. The strategy provides direct access to the correct oxidation level of the products. The combination of an organocatalyst guanidine superbase, a tertiary amine base, and a dehydrating agent was necessary for the successful Henry-Michael- dehydration cascade to form the phenanthrene motif. The required selective aliphatic nitro reduction could only be achieved under heterogeneous transfer-hydrogenation conditions.
