1020850-41-2Relevant academic research and scientific papers
The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones: Synthesis of (+)-paeonilactone B
Edwards, Michael G.,Kenworthy, Martin N.,Kitson, Russell R. A.,Scott, Mark S.,Taylor, Richard J. K.
, p. 1935 - 1937 (2008/12/22)
(Chemical Equation Presented) Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/ Horner-Wadsworth-Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ- butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B.
The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/Olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B
Edwards, Michael G.,Kenworthy, Martin N.,Kitson, Russell R. A.,Perry, Alexis,Scott, Mark S.,Whitwood, Adrian C.,Taylor, Richard J. K.
experimental part, p. 4769 - 4783 (2009/05/27)
A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to α-alkylidene-γ-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 π-allyl intermediate. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
