Synthesis of 4-hydroxy-15-oxaandrost-4-en-3-one and other potential aromatase inhibitors from sandaracopimaric acid

Abstract

The stereoselective synthesis of 4-substituted androstenes (8β,14α)30 and 36 related to inhibitors of the enzyme aromatase and 5α-reductase has been achieved in a short-step sequence from sandaracopimaric acid. The synthetic strategy is the stereoselective construction of ring D, and the appropriate modification of the A-ring diterpene functionality to the enone system found in the aromatase inhibitors. A parallel sequence is developed to obtain the isomers (8α,14β)31 and 41.