Journal
TETRAHEDRON-ASYMMETRY
Volume 17, Issue 9, Pages 1415-1419Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2006.04.023
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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 in three subsequent steps in 56% chemical yield. (c) 2006 Elsevier Ltd. All rights reserved.
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