Synthesis of 7β-hydroxy-epiandrosterone

[Display omitted] ▶ A highly stereoselective synthesis of 7β-hydroxy-epiandrosterone ( 6) – strongly anti-inflammatory compound – in 63% overall yield starting from 3β-acetoxy-17,17-(ethylenedioxy)-5-androsten ( 1) was described. This very efficient synthesis was conducted in a reproducible manner at scales ranging from 0.2 to 1 g of final compound. The synthesis of 7β-hydroxy-epiandrosterone ( 6) possessing strong anti-inflammatory properties was achieved starting from 3β-acetoxy-17,17-(ethylenedioxy)-5-androsten ( 1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7β-hydroxy-epiandrosterone in 63% overall yield.