Subject(s)
18-Hydroxycorticosterone/analogs & derivatives , 18-Hydroxydesoxycorticosterone/analogs & derivatives , Aldosterone/analogs & derivatives , Corticosterone/analogs & derivatives , Desoxycorticosterone/analogs & derivatives , 18-Hydroxycorticosterone/chemical synthesis , 18-Hydroxydesoxycorticosterone/chemical synthesis , Aldosterone/chemical synthesis , Gas Chromatography-Mass Spectrometry , Oxidation-ReductionABSTRACT
3 alpha,18,21-Trihydroxy-5 beta-pregnan-20-one 18 leads to 20-hemiacetal (18-hydroxy-tetrahydro-DOC) has been prepared from 3 alpha-acetoxy-5 beta-pregnan-20-one by reduction to the 20 beta-alcohol, application of the 'hypoiodite' reaction [Pb(OAc)4-I2-hv] with subsequent steps leading to the 18-hydroxy-20-ketone (as hemiacetal), and C-21 acetoxylation [Pb(OAc)4] followed by hydrolysis.
Subject(s)
18-Hydroxydesoxycorticosterone/analogs & derivatives , Desoxycorticosterone/analogs & derivatives , 18-Hydroxydesoxycorticosterone/chemical synthesisABSTRACT
Hypoiodite photolysis of 3beta-acetoxy-5-pragnen-20beta-olgave 3beta-acetoxy-5-pregnene-18,20-lactone in 46% yield. Lithium aluminum hydride reduction of the latter afforded 3beta, 18,20beta-trihydroxy-5-pregnen (91% yield) which, on Oppenauer oxidation, was converted to 18-hydroxyprogesterone (66%). Lead tetraacetate oxidation followed by mild saponification gave 18-hydroxydeoxycorticosterone (58%) yield).
