Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R.
An enantioselective synthesis of SNAP-7941, a potent melanin concentrating hormone receptor antagonist, was achieved by using two organocatalytic methods. The first method utilized to synthesize the enantioenriched dihydropyrimidone core was the Cinchona alkaloid-catalyzed Mannich reaction of beta-keto esters to acylimines and the second was the chiral phosphoric acid-catalyzed Biginelli reaction. Completion of the synthesis was accomplished via selective urea formation at the N3 position of the dihydropyrimidone with the 3-(4-phenylpiperidin-1-yl)propylamine side chain fragment. The synthesis of SNAP-7921 highlights the utility of asymmetric organocatalytic methods in the construction of an important class of chiral heterocycles.
Goss
Jennifer M
JM
Department of Chemistry, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, USA.
Schaus
Scott E
SE