Enantioselective synthesis of an HCV NS5a antagonist.
A concise, enantioselective synthesis of the HCV NS5a inhibitor MK-8742 (1) is reported. The features of the synthesis include a highly enantioselective transfer hydrogenation of an NH imine and a dynamic diastereoselective transformation. The synthesis of this complex target requires simple starting materials and nine linear steps for completion.
Department of Process Chemistry, Merck and Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
Ian K
IK
Mangion
Cheng-yi
CY
Chen
Hongmei
H
Li
Peter
P
Maligres
Yonggang
Y
Chen
Melodie
M
Christensen
Ryan
R
Cohen
Ingyu
I
Jeon
Artis
A
Klapars
Shane
S
Krska
Hoa
H
Nguyen
Robert A
RA
Reamer
Benjamin D
BD
Sherry
Ilia
I
Zavialov
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017361:Viral Nonstructural Proteins / Q000037:antagonists & inhibitors*; D012324:RNA-Dependent RNA Polymerase
D001572:Benzofurans; D007093:Imidazoles; D007097:Imines; D017361:Viral Nonstructural Proteins; C000589335:elbasvir; C087036:NS-5 protein, hepatitis C virus; D012324:RNA-Dependent RNA Polymerase