Formamide → (2S,5S,6S,14R,15S,16S)-2-(2-hydroxyacetyl)-14-methyl-17-oxapentacyclo[14.2.1.01,5.06,15.09,14]nonadec-9-en-11-one

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Reaction Steps

18-deoxyaldosterone was prepared by acid-catalyzed dehydration of 18-hydroxycorticosterone, the latter having been, in turn, prepared biosynthetically employing slices of aldosterone-producing adrenal tissue [Ulick et al, Methods in Enzymology, 36, p. 503 (1975)]. The 11,18-diol (1.0 mg.) in 10 ml 1,2-dichloroethane saturated with p-toluenesulfonic acid was heated under reflux for 30 minutes. The solvent was washed with dilute sodium carbonate and water, dried and evaporated. Chromatographic analysis of the residue revealed 18-deoxyaldosterone as the major product of 18-hydroxycorticosterone along with small amounts of starting material and its etiolactone derivative. 18-deoxyaldosterone migrated at 1.06 (±0.02) the rate of 11-dehydrocorticosterone in the toluene/formamide or methylcyclohexane:toluene (1:1)/formamde paper chromatographic systems. Its properties agreed with those of reference samples prepared by a published method [Kondo et al, JACS 87, 4655 (1965)]. Its 21-acetylated derivative prepared in the usual way with acetic anhydride:pyridine migrated at a slightly faster rate (1.05 ±0.02) than 21-acetoxy-11-dehydrocorticosterone in methylcyclohexane:toluene (1:1)/formamide.

Provenance & Evidence