Tetrahedron: Asymmetry

Enantioselective synthesis of (R)-(−)-praziquantel (PZQ)

P Roszkowski, JK Maurin, Z Czarnocki

文献索引：Roszkowski, Piotr; Maurin, Jan K.; Czarnocki, Zbigniew Tetrahedron Asymmetry, 2006 , vol. 17, # 9 p. 1415 - 1419

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被引用次数: 59

摘要

Praziquantel 8 (2-cyclohexylcarbonyl-1, 2, 3, 6, 7, 11b-hexahydro-4H-pyrazino [2, 1-a] isoquinoline-4-one), a powerful anti-worm drug, has been synthesized in its enantiopure form via asymmetric transfer hydrogenation according to the Noyori protocol. Initially, the reduction of prochiral imine 4 afforded product 5 in 62% ee, but a single crystallization amplified the enantiomeric purity to 98% ee. The final (R)-(−)-praziquantel 8 was prepared ...