| Abstract
| - The 1-azadiene hetero Diels−Alder reaction of silylated enol oximes with alkynes was investigated andwas optimized to furnish 2,5,6-trisubstituted 3-hydroxypyridines in high yields in one simple operation.Importantly, monosubstituted alkynyl ketones were found to lead to the formation of the 6-isomer withexceptional regioselectivity (>95:5). This methodology was applied to a scaleable synthesis of the corestructure of the potent antibiotic nosiheptide. Protecting groups were optimized, which led to aracemization-free seven-step synthesis of the key building block.
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