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Chemistry of Natural Compounds

, Volume 16, Issue 4, pp 383–386 | Cite as

Transformed steroids. 118. The geometric isomerism of 20-ethoxycarbonylhydrazones of 3β-hydroxy-16,17α-cyclopropanopregn-5-en-20-one

  • A. V. Kamernitskii
  • A. M. Turuta
  • Ngo Tkhi Mai An'
Article
  • 21 Downloads

Abstract

In the reaction of the 3β-acetate of 3β-hydroxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (I) with ethoxycarbonylhydrazine in AcOH at 20°C (exposure for up to 6 days), a chromatographically separable equilibrium mixture of the 20Z-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (II), with mp 190–195°C, and the 20E-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (III) with mp 186–193°C (ratio 2:1) is obtained. The geometric isomers obtained are distinguished by IR, PMR, and CD spectroscopy. It has been shown that the observed geometric isomerism takes place via an intermediate enehydrazine form.

Keywords

Hydrazones AcOH Geometric Isomerism HOAc Furostanol 

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Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • A. V. Kamernitskii
  • A. M. Turuta
  • Ngo Tkhi Mai An'

There are no affiliations available

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