Synthesis of heterocycles related to ellipticine.

  • Andrew Popplestone

Student thesis: Doctoral ThesisPhD


The work described in this thesis was conducted between June 1980 and January 1983 and is concerned with the development of potential synthetic approaches to the pyrido [4,3-b] fluorene ring system. The specific compound we required was 5,11-diraethyl-9-hydroxypyrido[4,3-b] fluorene which we hoped would exhibit the same type of DNA intercalating and antitumour activity in vivo as 9-hydroxyellipticine. Various strategies are described. Initial attempts were centred around the synthesis of the appropriately substituted fluorene compound 1,4-dimethyl-6-methoxyfluorene. Later strategies involved the coupling of appropriate indan and pyridine fragments followed by attempts to form the C ring in the last steps. The last effort involved attempted coupling of an isoquinoline to an anisole, which, if it had been successful would have required intramolecular ring closure of the B ring in the final stages. The unsuccessful coupling reaction was not investigated as thoroughly as we would have liked due to a lack of time and it is in this area where a little more research could well result in this project reaching a satisfactory conclusion.
Date of Award1983
Original languageEnglish
Awarding Institution
  • University of Bath

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