2-(Chloromethyl)-3-tosylpropene as useful reagent for the general synthesis of functionalized 2-substituted 1,3-dienes. Application to the synthesis of (±)-ipsenol

Article abstract of DOI:10.1016/S0040-4039(00)79227-6

The reaction of the monolithium derivative of 2-(chloromethyl)-3-tosylpropene (2) with bromomethyltrimethylsilane affords the β-silyl sulfone 7, which after nucleophilic substitution followed by fluoride induced β-elimination of tosyltrimethylsilane gives 2-substituted conjugated dienes 1. When compound 7 reacts first with zinc in the presence of isovaleraldehyde and then with tetrabutylammonium fluoride racemic ipsenol (10), an aggregation pheromone of the bark beetle Ips paraconfusus Lanier, is prepared.