Ritter-reaction on steroids1 1 This paper forms Part 33 of the series Steroids and Part 3 of Ritter-reaction on Steroids, Part 32: Gy. Schneider, E. Meskó, L. Hackler, Gy. Dombi, D. Zeigan and G. Engelhardt, J. Chem. Soc. Perkin Trans I in press, and Part 2: see Ref. 17. Ring expansion of steroid oxethans into dihydrooxazines

Gyula Schneider, Lászlzó Hackler, Pál Sohár

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Abstract

The 3β-acetoxy-16β,17β-epoxymethyleneandrost-5-ene (1) transforms into the dihydrooxazine condensed to the sterane skeleton (4a,b,c,e,g,i) in a ring-expansion reaction with alkyl and aryl nitriles in the presence of HBF4- diethyletherate The 3β-acetoxy-16α, 17α-epoxymethyleneandrost-5-ene (9) undergoes a Wagner-Meerwein rearrangement under similar conditions.

Original languageEnglish
Pages (from-to)3377-3386
Number of pages10
JournalTetrahedron
Volume41
Issue number16
DOIs
Publication statusPublished - 1985

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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