Structure and stereochemistry of the monobromotigogenins

J. P. Kutney, W. Cretney, George Pettit, J. C. Knight

Research output: Contribution to journalArticle

6 Citations (Scopus)

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
StatePublished - 1964
Externally publishedYes

Fingerprint

Spirostans
Stereochemistry
Bromine
Halogenation
Isomers
Mass spectrometry
Mass Spectrometry
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Biochemistry

Cite this

Kutney, J. P., Cretney, W., Pettit, G., & Knight, J. C. (1964). Structure and stereochemistry of the monobromotigogenins. Tetrahedron, 20(9), 1999-2006.

Structure and stereochemistry of the monobromotigogenins. / Kutney, J. P.; Cretney, W.; Pettit, George; Knight, J. C.

In: Tetrahedron, Vol. 20, No. 9, 1964, p. 1999-2006.

Research output: Contribution to journalArticle

Kutney, JP, Cretney, W, Pettit, G & Knight, JC 1964, 'Structure and stereochemistry of the monobromotigogenins', Tetrahedron, vol. 20, no. 9, pp. 1999-2006.
Kutney JP, Cretney W, Pettit G, Knight JC. Structure and stereochemistry of the monobromotigogenins. Tetrahedron. 1964;20(9):1999-2006.
Kutney, J. P. ; Cretney, W. ; Pettit, George ; Knight, J. C. / Structure and stereochemistry of the monobromotigogenins. In: Tetrahedron. 1964 ; Vol. 20, No. 9. pp. 1999-2006.
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