Synthesis of the mannosidase inhibitors swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine

  • Carpenter N
  • Fleet G
  • Cenci di Bello I
 et al. 
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Abstract

4,5-Anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol is a divergent intermediate for the efficient and practical syntheses of 1,4-dideoxy-1,4-imino-D-mannitol, swainsonine and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine. The effect on glycosidases of the ring contracted swainsonines is reported. © 1989.

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Authors

  • Neil M. Carpenter

  • George W.J. Fleet

  • Isabelle Cenci di Bello

  • Bryan Winchester

  • Linda E. Fellows

  • Robert J. Nash

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