The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B

Michael G. Edwards, Martin N. Kenworthy, Russell R. A. Kitson, Alexis Perry, Mark S. Scott, Adrian C. Whitwood, Richard J. K. Taylor

Research output: Contribution to journalArticlepeer-review

Abstract

A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to alpha-alkylidene-gamma-butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran-2,5-diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)-paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium-catalysed variant proceeding by way of a pi-allyl intermediate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

Original languageEnglish
Pages (from-to)4769-4783
Number of pages15
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
Publication statusPublished - Oct 2008

Keywords

  • tandem reactions
  • phosphonates
  • Michael addition
  • Horner-Wadsworth-Emmons
  • lactones
  • ONE-POT SYNTHESIS
  • PAEONILACTONE-B
  • ENANTIOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • SESQUITERPENE LACTONES
  • TANDEM OXIDATION
  • ALDEHYDES
  • ROUTE
  • CORE
  • STEREOCHEMISTRY

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