Chemistry of Natural Compounds

, Volume 18, Issue 1, pp 59–66 | Cite as

Transformed steroids. 123. Synthesis of 5α(H)- and 5α(OH)-6-ketosteroids with an additional 17α,20ξ-dihydroxytetrahydropyran ring E

  • A. V. Kamernitskii
  • V. G. Levi
  • I. G. Reshetova
  • V. S. Bogdanov
  • V. A. Pavlov
  • E. G. Cherepanova


The paper is devoted to the synthesis of 3,17α,20-trihydroxy-16β,23-epoxy-21,24-dinor-5αH-cholan-6-one and 3,5α,17α,20-tetrahydroxy-16β,23-epoxy-21,24-dinorcholan-6-one and derivatives of them. It has been shown that the reduction of 3,17α-dihydroxy-16β,23-epoxy-21,24-dinorchol-5-en-20-one with sodium tetrahydroborate and with diborane takes place stereospecifically with different spatial directivities: in the products of diborane reduction, ring E exists in the boat form, as has been shown by1H and13C NMR methods. The trans linkage of rings A/B in the modified steroids has been confirmed by their circular dichroism spectra.


EtOAc DMFA B2H6 Matrine Diborane 


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Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • A. V. Kamernitskii
  • V. G. Levi
  • I. G. Reshetova
  • V. S. Bogdanov
  • V. A. Pavlov
  • E. G. Cherepanova

There are no affiliations available

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