Tetrahedron: Asymmetry

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

P Roszkowski, JK Maurin, Z Czarnocki

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

Full Text: HTML

Citation Number: 59

Abstract

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 ...

Related Articles:

3-Aroylmethylene-2, 3, 6, 7-tetrahydro-1 H-pyrazino [2, 1-a] isoquinolin-4 (11b H)-ones as Potent Nrf2/ARE Inducers in Human Cancer Cells and AOM-DSS Treated …

[Xi, Mei-Yang; Jia, Jian-Min; Sun, Hao-Peng; Sun, Zhong-Ying; Jiang, Jie-Wei; Wang, Ya-Jing; Zhang, Min-Ye; Zhu, Jun-Feng; Xu, Li-Li; Jiang, Zheng-Yu; Xue, Xin; Ye, Ming; Yang, Xi; Gao, Yuan; Tao, Lei; Guo, Xiao-Ke; Xu, Xiao-Li; Guo, Qing-Long; Zhang, Xiao-Jin; Hu, Rong; You, Qi-Dong Journal of Medicinal Chemistry, 2013 , vol. 56, # 20 p. 7925 - 7938]

3-Aroylmethylene-2, 3, 6, 7-tetrahydro-1 H-pyrazino [2, 1-a] isoquinolin-4 (11b H)-ones as Potent Nrf2/ARE Inducers in Human Cancer Cells and AOM-DSS Treated …

[Xi, Mei-Yang; Jia, Jian-Min; Sun, Hao-Peng; Sun, Zhong-Ying; Jiang, Jie-Wei; Wang, Ya-Jing; Zhang, Min-Ye; Zhu, Jun-Feng; Xu, Li-Li; Jiang, Zheng-Yu; Xue, Xin; Ye, Ming; Yang, Xi; Gao, Yuan; Tao, Lei; Guo, Xiao-Ke; Xu, Xiao-Li; Guo, Qing-Long; Zhang, Xiao-Jin; Hu, Rong; You, Qi-Dong Journal of Medicinal Chemistry, 2013 , vol. 56, # 20 p. 7925 - 7938]

More Articles...