18-Substituted steroids. Part 8. An improved synthesis of 11β,18,21-trihydroxypregn-4-ene-3,20-dione (‘18-hydroxycorticosterone’)

Abstract
‘18-Hydroxycorticosterone’(1) has been prepared from 11β-formyloxy-20-hydroxypregn-4-en-3-one (6) by application of the ‘hypoiodite’ series of reactions [Pb(OAc)4–I2; oxidation; solvolysis], followed by acetoxylation at C-21 by lead tetra-acetate in acetic acid. Alkaline hydrolysis then gave 18-hydroxycorticosterone.

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