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Furan‐Derived Chiral Bicycloaziridino Lactone Synthon: Collective Syntheses of Oseltamivir Phosphate (Tamiflu), (S)‐Pipecolic acid and its 3‐Hydroxy Derivatives
Authors:Subhash P Chavan  Appasaheb L Kadam  Shrikrishna S Shinde  Rajesh G Gonnade
Abstract:A unified synthetic strategy for oseltamivir phosphate (tamiflu), (S)‐pipecolic acid, and its 3‐hydroxy derivatives from furan derived common chiral bicycloaziridino lactone synthon is described here. Key features are the short (4‐steps), enantiopure, and decagram‐scale synthesis of common chiral synthon from furan and its first‐ever application in the total synthesis of biologically active compounds by taking the advantages of high functionalization ability of chiral synthon.
Keywords:Aziridine synthon  Chiral auxiliary  Collective synthesis  Pipecolic acid  Tamiflu
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