Synthesis of 7β-hydroxy-epiandrosterone

Add time:08/04/2019    Source:sciencedirect.com

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.

▶ 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.

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