Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation

MSM Timmer, EM Dangerfield, JMH Cheng, SA Gulab…

Index: Timmer, Mattie S.M.; Dangerfield, Emma M.; Cheng, Janice M.H.; Gulab, Shivali A.; Stocker, Bridget L. Tetrahedron Letters, 2011 , vol. 52, # 37 p. 4803 - 4805

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Citation Number: 7

Abstract

A remarkably efficient synthesis of the biologically important iminosugar 1- deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate- containing piperidine skeleton over its five-membered counterpart.

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