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Synlett 1998; 1998(12): 1375-1377
DOI: 10.1055/s-1998-1965
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Synthesis of (+/-)-Oxohexahydrofuro[3,2-b]pyrroles (Pyrrolidine-trans-lactones) Using Acyl-Iminium Chemistry

Simon J. F. Macdonald* , Julie E. Spooner, Michael D. Dowle
  • *Enzyme Chemistry II, GlaxoWellcome Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK; Fax + (0) 1438 763 616
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Publication History

Publication Date:
31 December 2000 (online)

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In a new synthesis of pyrrolidine-trans-lactones, an acyliminium pyrrolidine reacts with silyl ketene acetals. This reaction selectively generates C2, C3 trans stereochemistry.

pyrrolidine-trans-lactone - acyl-iminium - ketene acetal - bromohydrin diol