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Synlett 2000; 2000(5): 0625-0626
DOI: 10.1055/s-2000-6592
DOI: 10.1055/s-2000-6592
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A Short Total Synthesis of Cerpegin by Intramolecular Hetero Diels-Alder Cycloaddition Reaction of an Acetylene Tethered Pyrimidine
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Publication History
Publication Date:
31 December 2000 (online)
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The electron poor 4,6-dichloropyrimidine-5-carbaldehyde, which is readily available, is used as a starting material for the synthesis of fused 2-chloropyridines. Chlorination transforms the aldehyde into the corresponding acid chloride, which can be functionalized with acetylene tethers. Intramolecular hetero Diels-Alder reactions at elevated temperatures afford the fused pyridines in varying yield. This reaction sequence was applied to the total synthesis of cerpegin.
hetero Diels-Alder cycloaddition - pyrimidines - cerpegin