The readily available norbornanone (2) gave a mixture of the lactones (3) and (4) on peracid oxidation, the minor component (4) being removed by treatment with aqueous alkali; conversion of (3) into (6) was performed so as to minimise silyl group scrambling, and the alcohol (6) was transformed into (±) prostaglandin D2 methyl ester (9) by oxidation followed by deprotection using HF in acetonitrile.
D. P. Reynolds, R. F. Newton and S. M. Roberts, J. Chem. Soc., Chem. Commun., 1979, 1150 DOI: 10.1039/C39790001150
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