Structure and stereochemistry of the monobromotigogenins

J. P. Kutney, W. Cretney, G. R. Pettit, J. C. Knight

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Bromination of desoxytigogenin has been found to yield two isomeric 23-bromo-5α-25R-spirostans. The corresponding 3β-acetoxy-23-bromo-5α-25R-spirostans were also prepared from tigogenin actetate. A combination of physical methods based on mass spectrometry and NMR measurements, at 60- and 100-mc/s, have been used to confirm attack by bromine at C-23 of the spiroketal system. The configuration of each epimeric pair (at C-23, cf. III and IV) of isomers was also determined.

Original languageEnglish (US)
Pages (from-to)1999-2006
Number of pages8
JournalTetrahedron
Volume20
Issue number9
DOIs
StatePublished - 1964
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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