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Synthesis of enantiopure furo[2,3-b]pyrroles

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Identifiers
DOI: 10.1016/j.tetlet.2014.08.080
Keywords
  • Furo[2
  • 3-B]Pyrroles
  • Garcinia Acid
  • Cyclic N-Acyl Hemiaminal
  • 3-Substituted And 3
  • 4-Disubstituted Pyrrolidinediones

Abstract

Abstract A simple method for the preparation of enantiopure furo[2,3-b]pyrroles, a rare class of concave bicyclic nitrogen and oxygen heterocycle, in promising yield has been developed. The 3-substituted pyrrolidinediones prepared from (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (Garcinia acid) have been cyclized diastereo as well as enantioselectively to furo[2,3-b]pyrroles. The cyclization follows Baldwin’s rule.

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