Novel preparation of dihydrooxazines condensed to ring D of the estrane skeleton

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Abstract

The reactions of cis-16-azidomethyl,17-hydroxyestrone derivatives with a range of aldehydes under the conditions of the Schmidt reaction were examined. The 16β-azidomethyl,17β-hydroxy isomer resulted in 5,6-dihydro-4H-1,3-oxazine fused to the estrane skeleton. This method allowed preparation of the 5,6-dihydro-4H-1,3-oxazine condensed to positions 16α, 17α of the estrone, the isomeric (2R)5,6-dihydro-2H-1,3-oxazine also being formed stereoselectively.

Original languageEnglish
Pages (from-to)1077-1080
Number of pages4
JournalSynlett
Issue number7
DOIs
Publication statusPublished - 2002

Keywords

  • Dihydrooxazines
  • Lewis acids
  • Ring closure
  • Stereoselective synthesis
  • Steroids

ASJC Scopus subject areas

  • Organic Chemistry

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