285991-63-1Relevant articles and documents
A short total synthesis of cerpegin by intramolecular hetero Diels-Alder cycloaddition reaction of an acetylene tethered pyrimidine
Tarasov, Evgeniy V.,Henckens, Anja,Ceulemans, Erik,Dehaen, Wim
, p. 625 - 626 (2007/10/03)
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.