110316-93-3Relevant academic research and scientific papers
Regiospecific Functionalization of Dimetalated Isopropenylacetylene, a Synthetic Equivalent of the Isoprene "Anion". An Efficient Synthesis of the Bark Beetle Pheromones (+/-)-Ipsenol and (+/-)-Ipsdienol
Klusener, Peter A. A.,Kulik, Willem,Brandsma, Lambert
, p. 5261 - 5266 (2007/10/02)
Regiospecific (mono)functionalization of dilithiated isopropenylacetylene LiCCC(=CH2)CH2Li with a large number of electrophilic reagents ("E+")gave the compounds HCCC(=CH2)CH2E in high yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O, followed by partial reduction of the triple bond with activated zinc powder, gave the bark beetle pheromones ipsenol and ipsdienol, respectively, in >55percent overall yields.
