Jenkinson, Julian John (1992) Tandem cyclisations towards indole alkaloids. University of Southampton, Doctoral Thesis.
Abstract
A variety of approaches to an intermediate for the proposed formation of the quebrachidine skeleton and ultimately the total synthesis of the monoterpenoid indole alkaloid ajmaline are described. Initial studies involved the formation of a model tandem cyclisation precursor using an acetylenic dianion technique, after attempts utilizing isonitrile, dithiane, and titanium chemistry had proved unsuccessful. The model system was subjected to radical and palladium mediated cyclisation reactions. In the former case this produced two novel tetracycles resulting from 5-exo, 6-endo tandem ring closure. The cyclisation precursor for the ajmaline system was similarly formed and subjected to the same radical conditions. This led to a 5-exo, 6-endo tandem cyclisation forming a fused ring tetracycle which is a useful intermediate towards the afore-mentioned goals.
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