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Synlett 2000; 2000(5): 0625-0626
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

Evgeniy V. Tarasov* , Anja Henckens, Erik Ceulemans, Wim Dahaen
  • *Department of Chemistry, Celestijnenlaan 200F, 3001 Heverlee (Leuven) Belgium; Fax 32 16 32 79 90; E-mail: wim.dehaen@chem.kuleuven.ac.be
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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