Russian Chemical Bulletin

, Volume 46, Issue 9, pp 1611–1614 | Cite as

Synthesis of 6α-methyl-16α,17α-cyclohexano-19-norprogesterone from a 19-methyl-6-desmethyl precursor

  • I. S. Levina
  • L. E. Kulikova
  • V. S. Bogdanov
Chemistry of Natural Compounds and Bioorganic Chemistry


After prolonged refluxing of 19-tosyloxy-16α,17α-cyclohexanopregn-5-en-3β-ol-20-one (3) with NaI in 2-propanol, the initially formed 19-iodo derivative (4) undergoes supraface migration of the CH2I group from the C(10) atom to the C(6) atom, probably through involvement of a homoallyl cation. The resulting 6β-iodomethyl-16α,17α-cyclohexano-19-norpregn-5(10)-en-3β-ol (5) was transformed in three steps into 6α-methyl-16α,17α-cyclohexano-19-norprogesterone (6α-methyl-19-nor-D′ 6-pentarane,8). The transformation of compound5 into the target product8 also gave a side product, a pentarane with aromatic ringA (10), which was isolated and characterized by spectroscopic methods.

Key words

6-methyl-19-norpentaranes synthesis transformations homoallylic rearrangement 


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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • I. S. Levina
    • 1
  • L. E. Kulikova
    • 1
  • V. S. Bogdanov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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