Synthesis and NMR study of adamantane derivatives

Pál Sohár, János Kuszmann, Ágnes Néder

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Abstract

For the synthesis of modified aminoglycosides dimethyl biciclo[3,3,1]nonane-2,6-dione-3,7-dicarboxylate (1) was reduced with LiAlH4 and subsequently mesylated to give the corresponding 2,6-dimesyloxy-3,7-dimethylene derivative 3. Diene 3 underwent addition and simultaneous cyclisation when treated with different reagents, yielding 1,3,4,8-tetrasubstituted adamantane derivatives 6,7 and 8. The steric arrangement of the different substituents in the new compounds was established by NMR investigation. Correlation between structure and the spectral data was studied, first of all the limits of the additivity of substituent effects in the C-13 NMR spectra. The additivity is valid for the non-substituted bridghead atoms and for the methylene carbons, but in the case of the substituted tertiary carbons a significant non-additivity was observed making the determination of the configuration possible.

Original languageEnglish
Pages (from-to)2523-2532
Number of pages10
JournalTetrahedron
Volume42
Issue number9
DOIs
Publication statusPublished - 1986

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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