The systhesis of A-norandrostane-3-oxo-16β-carboxylate
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O629.2

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    Abstract:

    A-norandrostane-3-oxo-16β-carboxylate was synthesized from 3-oxo-4-androstene-17β-carboxylate by Beayer-Villger oxidation and two independent chemical operation,which were sodium methoxide promoted ring contraction rearrangement and decarbonylation, the total yield was 39.2 %.By controlling the amount of oxidant metachloroperbenzoic acid (m-CPBA) and using ZnCl2 as Lewis acid,the yield of the product of Beayer-Villger oxidation 3-oxo-4-androstene-17β-carboxylate was 92.3 %. 3-oxo-4-androstene-17β-carboxylate was converted to A ring constracted β-oxo aldehyde in the effect of sodium methoxide in dry tetrahydrofunan,,then it was decarbonylated by NaOH aqueous solution ,the product A-norandrostane-3-oxo-16β-carboxylate was prepared,its yield was 42.5 %.The method offers a new and unique synthetic route for preparation of A-norsteroidal compound.

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History
  • Received:March 06,2013
  • Revised:April 19,2013
  • Adopted:April 24,2013
  • Online: July 29,2013
  • Published:
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