Monatshefte für Chemie / Chemical Monthly

, Volume 128, Issue 12, pp 1297–1300 | Cite as

Hydroxylation of a vitamin D A-ring fragment

Short communication
  • C. Hamon
  • J. D. Soilan-Rodriguez
  • H. Kalchhauser
  • W. Reischl
Organische Chemie Und Biochemie

Summary

When the benzoate of (S)-(Z)-2-(5-(tert-butyldimethylsiloxy)-2-methylencyclohexyliden)-ethanol (5) is treated with 2.5 equivalents of Hg(OOCCF3)2 in dryTHF, a smooth and selective allylic hydroxylation occurs. The C-1 functionalized vitamin D A-ring synthon6 is isolated in 65 to 70% yield in a single step.

Keywords

Vitamin D Vitamin D A-ring fragment C-1 Hydroxylation Hg(OOCCF3)2 

Hydroxylierung eines Vitamin D A-Ring-Fragments (Kurze Mitt.)

Zusammenfassung

Umsetzung des Benzoats von (S)-(Z)-2-(5-(tert-Butyldimethylsiloxy)-2-methylencyclohexyliden)-ethanol (5) mit 2.5 Äquivalenten Hg(OOCCF3)2 in trockenemTHF führt zu einer selektiven allylischen Hydroxylierung. Damit ist das an C-1 funktionalisierte Vitamin D A-Ring-Fragment6 in einem einzigen Schritt in einer Ausbeute von 65 bis 70% zugänglich.

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References

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Copyright information

© Springer-Verlag 1997

Authors and Affiliations

  • C. Hamon
    • 1
  • J. D. Soilan-Rodriguez
    • 1
  • H. Kalchhauser
    • 1
  • W. Reischl
    • 1
  1. 1.Department of Organic ChemistryUniversity of ViennaViennaAustria

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