Traboulsi, Iman; Dange, Nitin S.; Pirenne, Vincent; Robert, Frederic; Landais, Yannick published the artcile< Enantioselective Total Synthesis of (+)-Eucophylline>, HPLC of Formula: 38487-85-3, the main research area is eucophylline total enantioselective synthesis free radical cyanation; Eucophylline; Monoterpene indole Alkaloid; cyclobutane; cyclobutene; cyclopropane; radical; sulfonyl-cyanation.
The total enantioselective synthesis of (+)-eucophylline (I) was achieved using as a key-structural motif a chiral piperidinone, II, bearing the natural product all-carbon quaternary stereocenter. The elaboration of the latter is based on two strategies relying on the free-radical carbo-cyanation and sulfonyl-cyanation resp. of enantiopure substituted cyclopropenes and cyclobutenes. Co- or Ni-boride reduction of the nitrile functional group along with the cyclopropane and cyclobutane ring-opening then led to the formation of the chiral piperidinone ring. Further elaboration of the latter into the key 1-azabicyclo[3.3.1]nonane motif followed by its coupling with a 2-cyanoaniline allowed the formation of the tetrahydrobenzo[b][1,8]-naphthyridine skeleton of I, which was finally accessible in 17 steps and 5.9% overall yield from 1,1-dibromobutene.
Chemistry – A European Journal published new progress about Cyanation. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, HPLC of Formula: 38487-85-3.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts