West, Robert Ian (1990) Synthetic approaches to Strychnos alkaloids. University of Southampton, Doctoral Thesis.
Abstract
Various approaches to an intermediate for the proposed synthesis of Strychnos alkaloids are described. Initial studies involved addition of carboxylic ester enolates to a suitable functionalised imine Chapter 3 describes the results of the reaction of imines with silyl ketene acetals under Lewis acid catalysis. The desired cycloaddition was not observed in these examples, with reaction leading to acyclic products. An attempted niobium coupling reaction is also described. The final chapter describes the use of a nitrone-olefin (3+2) cycloaddition reaction in an attempt to form the desired intermediate. Trial studies using ethyl vinyl ether as the dipolarophile led to the formation of a mixture of two diastereoisomeric isoxazolidines, which were used as a model system for radical cyclisation. This produced two novel tetracyclic ring systems, resulting from both 5-exo and 6-endo cyclisation.
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