113301-10-3Relevant academic research and scientific papers
18-Substituted Steroids. Part 13. Improved Preparation of the Metabolites of Aldosterone Reduced in Ring A
Kirk, David N.,Rajagopalan, Maruthiandan S.
, p. 1343 - 1346 (2007/10/02)
Protection of the side-chain of aldosterone as the 21-t-butyldimethylsilyl (TBDMS) ether was also found to mask the 20-oxo function, by effectively locking the tautomeric structure of aldosterone into its 11,18:18,20-diepoxy form.Catalytic hydrogenation of aldosterone 21-TBDMS ether gave the 5α- or the 5β-dihydro derivative depending on the choice of solvent.Subsequent reduction of the carbonyl group at C-3, with either 'K-selectride' to form the 3-axial alcohol or lithium tri-t-butoxyaluminium hydride to form the 3-equatorial alcohol, was found to proceed without attack on the side-chain, to give convenient routes to the four isomeric tetrahydroaldosterones.
