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Citation: JIANG Min, CUI Peng, YU Tao, YANG Fan, TANG Jie. Synthesis of 3β-Hydroxyandrost-4-en-6, 17-dione[J]. Chinese Journal of Applied Chemistry, ;2006, 23(12): 1422-1424. shu

Synthesis of 3β-Hydroxyandrost-4-en-6, 17-dione

1.
Department of Chemistry, East China Normal University, Shanghai 200062

Corresponding author: YANG Fan,
Received Date: 28 November 2005
Available Online: 8 February 2006
Fund Project: 上海市科委基础研究重点项目(04JC14032) (04JC14032)

3β-Hydroxyandrost-4-en-6,17-dione(3-OHAT),a non-androgenic aromatase inhibitor,was synthesized via a new process.With dehydroepiandrosterone acetate as starting material,the synthetic procedure included five steps: epoxidation of C=C bond with performic acid,ring opening of the epoxide with periodic acid,oxidation of 6-hydroxy by IBX,elimination of H₂O and hydrolysis of the ester.The total yield was up to 55%.The use of performic acid,an affordable and easily prepared reagent,in epoxidation led to quantitatively the target epoxide.The oxidation of the 1,2-diol by IBX provided the oxidative product with a high yield of 98.5%,moreover,the introduction of IBX avoided the use of chromic reagent,which leads to the tedious work-up for the product purification and environmental pollution.
- 3β-Hydroxyandrost-en-dione,
- IBX,
- synthesis
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