1107484-78-5Relevant articles and documents
Asymmetric synthesis of highly functionalized tetrahydropyran DPP-4 inhibitor
Xu, Feng,Zacuto, Michael J.,Kohmura, Yoshinori,Rosen, Jon,Gibb, Andrew,Alam, Mahbub,Scott, Jeremy,Tschaen, David
, p. 5422 - 5425 (2014)
A practical synthesis of a highly functionalized tetrahydropyran DPP-4 inhibitor is described. The asymmetric synthesis relies on three back-to-back Ru-catalyzed reactions. A Ru-catalyzed dynamic kinetic resolution (DKR) reduction establishes two contiguous stereogenic centers in one operation. A unique dihydropyran ring is efficiently constructed through a preferred Ru-catalyzed cycloisomerization. Hydroboration followed by a Ru-catalyzed oxidation affords the desired functionalized pyranone core scaffold. Finally, stereoselective reductive amination and subsequent acidic deprotection afford the desired, potent DPP-4 inhibitor in 25% overall yield. (Chemical Equation Presented).