Currently cancer chemotherapy, which is still in its infancy, is stimulating much interest, with over 250 new products as candidates for human clinical trials. Some of the more important alkaloids in this area are androcymbine, tylophorine and ellipticine and consequently the initial aim of this work was to find improved synthetic routes to these compounds. The use of aryl-aryl coupling to prepare natural products has opened a new field in organic chemistry and introduced many new techniques, one of which is electro-anodic oxidation. In the first part of this work some derivatives of tetrahydro-isoquinoline were subjected to electro-oxidation in an attempt to prepare androcymbine. The preparation of tylophorine from the alkaloid septicine through the use of photochemistry and aryl-aryl coupling is discussed in Part Two of this thesis. Finally, in the last part of this work new synthetic routes to the alkaloid ellipticine are described and the preparation of its 8-methoxy derivative is reported.
|Date of Award||1978|