Hydroxydihydroeremophilone (HDE) has been synthesized from eremophilone by two procedures. In one the kinetic enolate of 1,10-dihydroeremophilone was oxidised with molybdenum peroxide to the 8β-epimeride of HDE, which was then epimerised by acid to HDE. Alternatively the trimethylsilyl ether of the kinetic enolate could be oxidised by peracid to an α-trimethylsilyloxyketone, which was then hydrolysed by acid to HDE.
A. R. Pinder and W. D. Saunders, J. Chem. Soc., Perkin Trans. 1, 1978, 282 DOI: 10.1039/P19780000282
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