Synthetic efforts towards 6H - pyrido [4,3-b] carbazole derivatives.

  • David Watkins

Student thesis: Doctoral ThesisPhD


The work outlined in this thesis was conducted between October 1977 and September 1980 and is primarily concerned with the synthesis of ellipticine derivatives, which materials show promise as potential antitumour agents. At the time work commenced there was a need to develop an improved method of preparation for the starting material which is fundamental to the ellipticine synthesis favoured by workers at Bath. This synthesis is recognised as a versatile route to a variety of derivatives, but so far an efficient preparative method for the starting material - a pyridylethyl indole - has not been found. Alternative strategies are discussed here. The next section deals with the preparation of some new derivatives of ellipticine substituted in the 5-position with a variety of functional groups, and highlights some of the drawbacks of the known method which had previously not been encountered. The 13C nuclear magnetic resonance spectrum of ellipticine is discussed at some length in relation to the apparent regio-specificity of the reaction in which it is formed, and spectral data are compared with those of other workers. As yet, the assignment of 13C chemical shift values remains fairly empirical, but from comparison with model compounds a new interpretation of the ellipticine spectrum has been proposed. Finally, attempts to prepare 6 methyl-and 10-hydroxy-derivatives of ellipticine are described, the first of these involving a new synthetic route and alternative methods of preparation of 4-acetylpyridines.
Date of Award1982
Original languageEnglish
Awarding Institution
  • University of Bath

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