Amidyl radicals generated from tributylstannane mediated homolysis of O-acyl hydroxamic acid derivatives 5a-b undergo tandem cyclisations to give pyrrolizidinones 6a-c and indolizidinones 7a-b respectively while 5c-d undergo monocyclisation to give b-lactam 10a and g-lactam 11a respectively. On the other hand the reaction of 5d-f with Cu(OTf) 2 /DBN furnishes mixtures of reduction 10b, monocyclisation 10a and tandem cyclisation 9 products with the ratio dependant upon the nature of the O-acyl group and the solvent and concentration employed.
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