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 language | English |
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Pages (from-to) | 4769-4783 |
Number of pages | 15 |
Journal | European Journal of Organic Chemistry |
Issue number | 28 |
DOIs | |
Publication status | Published - 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