76976-60-8Relevant articles and documents
18-Substituted Steroids. Part 7. Synthesis and Structure of 11β,18-Epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one (3α,5β-Tetrahydroaldosterone)
Kirk, David N.,Miller, Barry W.
, p. 2818 - 2829 (2007/10/02)
3α,5β-Tetrahydroaldosterone (1) has been prepared from 21-deoxy-3α,5β-tetrahydroaldosterone 18-methyl ether 3-(tetrahydropyran-2-yl) ether (6).Kinetically controlled enolisation with lithium di-isopropylamide followed by treatment with chlorotrimethylsilane generated specifically the Δ20(21)-trimethylsilyl enol ether (17), which reacted with 3-chloroperbenzoic acid to give the 18-methyl ether-21-alcohol (18), which was converted into its 21-acetate (27).Acid solvolysis of the protecting groups at C-3 and -18 with anhydrous acetic acid, followed by mild alkaline hydrolysis with sodium hydrogencarbonate afforded 3α,5β-tetrahydroaldosterone (1) in 26percent overall yield.
