Total Synthesis of 0231B, an Inhibitor of 3α-Hydroxysteroid Dehydrogenase Produced by Streptomyces sp. HKI0231

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  • KOMODA Taichi
    <i>The United Graduate School of Agricultural Science, Gifu University</i>
  • SHINODA Yoshihiko
    <i>The United Graduate School of Agricultural Science, Gifu University</i>
  • NAKATSUKA Shin-ichi
    <i>The United Graduate School of Agricultural Science, Gifu University</i>

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タイトル別名
  • Total Synthesis of 0231B, an Inhibitor of 3.ALPHA.-Hydroxysteroid Dehydrogenase Produced by Streptomyces sp. HKI0231
  • Total Synthesis of 0231B an Inhibitor of 3 アルファ Hydroxysteroid Dehydrogenase Produced by Streptomyces sp HKI0231
  • Total Synthesis of 0231B, an Inhibitor of 3α-Hydroxysteroid Dehydrogenase Produced by<i>Streptomyces sp</i>. HKI0231

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抄録

  The new inhibitors of 3α-hydroxysteroid dehydrogenase, 0231A 1 and 0231B 2, have a unique benz[c,d]indol-3(1H)-one structure in their molecules. In our advanced studies on indole chemistry, we have developed an efficient synthetic method for benz[c,d]indol-3(1H)-one derivatives. We report here its application to the synthesis of 0231B in 10 steps (8.1% overall yield) from 6-methylindole 8 by introducing an acyl group into the 3-position of the indole nucleus, cyclization of the side chain at the 3-position to the 4-position and subsequent elimination of the phenyl group, and conjugate addition of the substituted phenyl group.<br>

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