Enantiomerically pure polyhydroxylated acyliminium ions. Synthesis of the glycosidase inhibitors (-)-swainsonine and (+)-castanospermine

SA Miller, AR Chamberlin

Index: Miller, Scott A.; Chamberlin, A. Richard Journal of the American Chemical Society, 1990 , vol. 112, # 22 p. 8100 - 8112

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Citation Number: 97

Abstract

Abstract: Hydroxylactams, which are useful precursors of acyl iminium ions for cationic cyclization, are most often prepared by hydride reduction of imides. This procedure is not directly applicable, however, to the enantioselective preparation of any highly substituted hydroxy lactam that would be derived from a meso imide, since such a reduction with the usual achiral agents must produce a racemic product. Two enantioselective methods of ...