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

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

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).

    Research areas

  • 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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