1,5-diketones from 3,4-dihydropyranones: An application in the synthesis of (±)-α-herbertenol

Article abstract of DOI:10.1016/S0040-4020(99)00495-0

An approach to 1,5-diketones involving the addition of organolithium reagents to 3,4-dihydropyranones is described. Good yields are obtained when reactions are quenched with trimethylsilyl chloride prior to hydrolytic work up and the organolithium reagent contains a Lewis basic group adjacent to the carbon to lithium bond. The method has been applied in a short synthesis of the fungicidal sesquiterpene (±)-α-herbertenol.