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A straightforward synthesis of (E)-δ-alkenyl-β,γ-unsaturated δ-lactones by a tandem ring-closing/cross-coupling metathesis process

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
44
Identifiers
DOI: 10.1016/j.tetlet.2003.09.056
Keywords
  • Metathesis
  • Lactones
  • Ring-Closure
  • Cross-Coupling
  • Isomerisation

Abstract

Abstract The access to ( E)-δ-alkenyl-β,γ-unsaturated δ-lactones starting from 3- O-(1,4-pentadienyl) 3-butenoate has been investigated by using a tandem process including two different metathesis reactions. By this way, new structures, isomers of natural compounds like argentilactone, were isolated in good yields. Reconjugation of the internal CC bond can be achieved under basic conditions to give α-pyrones.

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