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Synfacts 2005(2): 0261-0261
DOI: 10.1055/s-2005-916096
DOI: 10.1055/s-2005-916096
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
A New Reagent for the Hydrogenolysis of Bicyclic Endoperoxides
A. C. Spivey*, C. G. Mañas, I. Mann
Imperial College London, UK,, and GSK Tonbridge, Kent, UK
Further Information
Publication History
Publication Date:
25 October 2005 (online)
Significance
Polystyrene-bound N-methylthiourea 2 was prepared by refluxing aminomethylated polystylene 1 with 1.1 equivalent of methyl isothiocyanate (both are commercially available) in Et2O followed by extensive washing with anhydrous Et2O. Treatment of endoperoxide 4 with 1.5 equivalents of polystyrene-bound N-methylthiourea 2 in CH2Cl2 at 0 °C for 30 minutes followed by filtration and solvent evaporation gave γ-hydroxy enone 5. Protection of γ-hydroxy enone 5 by Ac2O/Et3N/DMAP and TBSOTf/2,6-lutidine/DMAP led to γ-acetoxy and γ-siloxy enones 6 and 7 in overall yields of 85% and 81%, respectively.