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Starting from R-(-)-carvone, a sequence of reactions has been developed for the enantioselective synthesis of key intermediates, which contain ether and hemiacetal bridges that are present in antifeedant clerodanes such as brevifloralactone and jodrellin.
The copper catalysed conjugate addition of methyl magnesium iodide to cyclohexenones and trapping of the enolate as its trimethylsilyl enol ether, followed by a trityl hexachloroantimonate (TrSbCl 6 ) catalysed Mukaiyama-reaction, was applied to R-(-)-carvone. This proved to be an efficient method for the preparation of C-2, C-3 functionalised chiral cyclohexanones. These compounds were converted...
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