| Title | Enantioselective Synthesis of SNAP-7941: Chiral Dihydropyrimidone Inhibitor of MCH1-R. | | Author(s) | Goss JM, Schaus SE | | Source | J Org Chem 2008 Sep 4. | | Abstract | 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. | | Language | ENG | | Pub Type(s) | JOURNAL ARTICLE
| | PubMed ID | 18767801 |
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