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• Synthesis

  Trestolone was prepared as follows: Using 19-norandrost-4,6-diene-17-acetoxy-3-one, one of the conjugated steroidal enones, as a starting material, 19-norandrost-4-ene-7-methyl-17-hydroxy-3-one (Trestolone) was prepared by dissolving 62.8 g of 19-norandrost-4,6-diene-17-acetoxy-3-one and 1.0 g of CuCl in 800 g of tetrahydrofuran. The mixture was heated to 50 °C, and 8 g of trimethylaluminum was added. The mixture was stirred for 6 hours, and then 50 g of water was added to the reaction system. The mixture was stirred for 2 hours, filtered, and the filtrate was evaporated to dryness under reduced pressure. The filtrate was purified by column chromatography to obtain 42.9 g of the product Trestolone (19-norandrost-4-ene-7-methyl-17-acetoxy-3-one), with a yield of 65%.
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