181651-50-3Relevant academic research and scientific papers
Biomimetic cyclization of enamide-containing polyenes as a new route to azapolycycles
Sen, Stephanie E.,Roach, Steven L.
, p. 6646 - 6650 (2007/10/03)
Enamide 4 was studied for its effectiveness as a polyene precursor in biomimetic cyclizations. While most conventional Lewis acids were poor cyclization promoters, FeCl3·6H2O initiated the conversion of 4 into tricycles 6 and 7 in excellent yield. The two isomeric products result from the cyclization of intermediate aldehyde 5 by either a chair or boat B-ring transition state. These results suggest that enamides may be incorporated into polyene precursors for the construction of larger azapolycycles such as azasteroids.
