Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

Alexander Kasal, Miloš Buděšínský, Jan Pelnař, Michael A. Bruck, Michael F. Brown

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor-5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor-5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.

Original languageEnglish (US)
Pages (from-to)2019-2034
Number of pages16
JournalCollection of Czechoslovak Chemical Communications
Volume64
Issue number12
DOIs
StatePublished - Dec 1999

Keywords

  • Absolute configuration
  • Antiandrogens
  • C
  • Conformation analysis
  • H
  • NMR Spectroscopy
  • Rearrangements
  • Solvolysis
  • Steroids
  • X-Ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

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