Hypervalent iodine in organic synthesis. A novel route to the dihydroxyacetone side-chain in the pregnene series
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 641-642
- https://doi.org/10.1039/c39810000641
Abstract
Treatment of pregnenolone (1) with PhIO 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).Keywords
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