SCHEDULED MAINTENANCE
Treatment of pregnenolone (1) with PhI![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
O and KOH in MeOH yields 3β,21-dihydroxypregn-5-en-20-one dimethyl acetal (2) from which a molecule of MeOH is lost to yield the C(17)–C(20) enol methyl ether (3) which may be epoxidized and hydrolysed to yield the C-17-dihydroxyacetone side-chain in the correct configuration as in 3β,17α,21-trihydroxypregn-5-en-20-one (4).
R. M. Moriarty, L. S. John and P. C. Du, J. Chem. Soc., Chem. Commun., 1981, 641 DOI: 10.1039/C39810000641
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