%0 Generic %A Hassan, Haitham %A Mohammed, Shireen %A Robert, Frédéric %A Landais, Yannick %D 2015 %T Total Synthesis of (±)-Eucophylline. A Free-Radical Approach to the Synthesis of the Azabicyclo­[3.3.1]­nonane Skeleton %U https://acs.figshare.com/articles/dataset/Total_Synthesis_of_Eucophylline_A_Free_Radical_Approach_to_the_Synthesis_of_the_Azabicyclo_3_3_1_nonane_Skeleton/2130433 %R 10.1021/acs.orglett.5b02218.s001 %2 https://acs.figshare.com/ndownloader/files/3764233 %K Eucophylline %K skeleton %K amidine %K Approach %K eucophylline %K 10 steps %K sequence %K cyclization %K azabicyclo %K olefin %K Azabicyclo %K bicyclic chloroenamine %K synthesis %K naphthyridine core %K SkeletonThe %K trisubstituted benzonitrile %K Total Synthesis %X The first total synthesis of eucophylline was reported in 10 steps and 10% overall yield. The naphthyridine core of eucophylline was prepared through the coupling between a strained azabicyclo­[3.3.1]­nonan-2-one and a trisubstituted benzonitrile, followed by a cyclization of the corresponding amidine. This coupling reaction was shown to proceed through a stable bicyclic chloroenamine intermediate. The azabicyclo­[3.3.1]­nonan-2-one skeleton was in turn accessible through a straightforward sequence including a free-radical three-component olefin carbo-oximation as a key step. %I ACS Publications