Synthesis of (2,3,1')-stegobinone, the pheromone of the drugstore beetle, with stereocontrol at C-2 and C-1'
1986; Elsevier BV; Volume: 42; Issue: 16 Linguagem: Inglês
10.1016/s0040-4020(01)87280-x
ISSN1464-5416
Autores Tópico(s)Sesquiterpenes and Asteraceae Studies
Resumo(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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