Transformed steroids. 115. Stability of nitrogen invertomers in steroido[16α,17α-d]-N-methoxyisoxazolidine series

  • A. V. Kamernitskii
  • I. S. Levina
  • V. M. Shitkin
  • B. S. Él'yanov
Organic Chemistry


  1. 1.

    The regiospecific 1,3-dipolar cycloaddition of Z- and E-nitronic esters to steroidal Δ16-olefins gives both of the possible diastereomers, which arise as the result of the exo and endo approach of the dipole.

  2. 2.

    In each pair of diastereomers one is unstable and undergoes transformation to the stable isomer of another pair.

  3. 3.

    The transformation of unstable stereoisomers to stable isomers represents inversion of the isoxazoline nitrogen atom, accompanied by conformational reorganization of the ciscoupled convertolike (five-membered) carbo- and heterocycles.



Nitrogen Ester Steroid Nitrogen Atom Stable Isomer 
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Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • A. V. Kamernitskii
    • 1
  • I. S. Levina
    • 1
  • V. M. Shitkin
    • 1
  • B. S. Él'yanov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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