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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 1: 241 - 245

DOI: https://doi.org/10.6023/cjoc201407007

Notes

Selective Synthesis of 7β-Hydroxyepiandrosterone

  • Huang Yanmin ,
  • Liu Liang ,
  • Qi Binbin ,
  • Zhao Dandan ,
  • Yang Lei ,
  • Gan Chunfang ,
  • Cui Jianguo
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  • a College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001;
    b Sichuan Welltzpharm Inc., Chengdu 610041

Received date: 2014-07-06

  Revised date: 2014-08-26

  Online published: 2014-09-12

Supported by

Project supported by the Natural Science Fundation of Education Department of Guangxi Province (No. 201202ZD059).

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Abstract

The 7β-hydroxyepiandrosterone (4) is a kind of compound possessing strong anti-inflammatory properties. Using dehydroisoandrosterone as starting material, 3β-acetoxy-7-oxodehydroisoandrosterone (3) was obtained by acetylation and oxidization. In the presence of Ni2+, compound 3 was selectively reduced to give compound 4, its 7-epimer, 7α-hydroxyepi- androsterone (5) and byproduct 6. The condition of selective reduction was investigated further. The structures of all compounds were characterized by IR, NMR and MS techniques.

Key words： dehydroisoandrosterone; 7β-epiandrosterone; 7α-epiandrosterone; selective reduction

Cite this article

Huang Yanmin , Liu Liang , Qi Binbin , Zhao Dandan , Yang Lei , Gan Chunfang , Cui Jianguo . Selective Synthesis of 7β-Hydroxyepiandrosterone[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 241 -245 . DOI: 10.6023/cjoc201407007

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