Preparation of 3-bromomethyl-3-butenal diethylacetal and its conversion into isoprenoid aldehydes derivatives

Abstract

The cyclopropanation of ethyl 3,3-diethoxypropionate with alkoxytitanacyclopropane reagents followed by the cleavage of the three-membered carbocycle in the formed cyclopropyl mesylate provided in a good yield 3-bromomethyl-3-butenal diethylacetal. The latter was brought into reactions of aldehyde allylation and cross-coupling with allyl halides in the intermediate stages at the generation of carbanionic intermediates. The conversion of compounds obtained into the corresponding β, γ- or α,β-unsaturated aldehydes demonstrated the opportunity of applying 3-bromomethyl-3-butenal diethylacetal as a C5-isoprenoid building block.