The epoxides of 2-alkylcyclopent-2-enones (I) react with acetic acid to give 5-acetoxy-2-alkylcyclopent-2-enones (II) which afford (±)-11-deoxy-10-hydroxyprostaglandins [(V) and (IX)]via conjugate-addition reactions. The 11-deoxy-10-hydroxyprostaglandin (IXa) readily undergoes base-catalysed autoxidation to the 11-deoxy-10-oxoprostaglandin (XIII).
M. P. L. Caton, G. Darnbrough, T. Parker, B. J. Peart, M. L. Podmore and T. L. Threlfall, J. Chem. Soc., Perkin Trans. 1, 1983, 319 DOI: 10.1039/P19830000319
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