Synthesis of (2S,3R,1'R)-stegobinone (cas 110996-50-4), the pheromone of the drugstore beetle, with stereocontrol at C-2 and C-1'

Add time:08/24/2019    Source:sciencedirect.com

(2S,3R,1'R)-Stegobinone [2,3-dihydro-2,3,5-trimethyl-6-(1'-methyl-2'-oxobutyl)-4H-pyran-4-one], the pheromone of Stegobium paniceum L., was synthesized with stereocontrol at C-2 and C-1' starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxy-2-methylpropanoate. The dihydro-γ-pyrone ring of the pheromone was constructed by an intramolecular acylation followed by acid-catalyzed cyclization.

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