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Synthesis of versatile bicyclo[5.4.0]undecane systems from tetrachlorocyclopropene

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
10
Identifiers
DOI: 10.1016/j.tetlet.2004.01.055
Keywords
  • Tetrachlorocyclopropene
  • Furan
  • Robinson Annulation
  • Bicyclo[5.4.0]Undecane

Abstract

Abstract 2,2,3,4-Tetrachloro-8-oxabicyclo[3.2.1]octa-2,6-diene, derived in a single step from the cyclocondensation of furan and tetrachlorocylopropene, serves as a key intermediate for the construction of bicyclo[5.4.0]undecane synthons. Conversion to a meso-1,3 diketone is followed by a high yielding Robinson annulation reaction. Studies on the reduction of the enone product reveals a powerful preference for formation of the cis-ring fusion.

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