Journal of Organic Chemistry p. 5261 - 5266 (1987)
Update date:2022-08-04
Topics: Characterization Final steps Protection and Deprotection Preparation of Dimetalated Isopropenylacetylene Regiospecific Functionalization Elaboration of the Molecule
Klusener, Peter A. A.
Kulik, Willem
Brandsma, Lambert
Regiospecific (mono)functionalization of dilithiated isopropenylacetylene LiC<*>CC(=CH2)CH2Li with a large number of electrophilic reagents ("E+")gave the compounds HC<*>CC(=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.
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