Asymmetric aldol condensation as a route to polypropionate derived pheromones.
The synthesis of the polypropionate-derived pheromones sitophilate (1) and sitophilure (2) are described using an asymmetric aldol condensation as the key step to adduct 6; compound 6 was smoothly converted to the antipodes of each pheromone. This procedure can be expanded to more complicated structures with the same type of syn configuration such as stegobinone (3) and serricornin (4).
DiBattista
J P
JP
Department of Chemistry, SUNY College of Environmental Science and Forestry, Syracuse, NY 13210, USA.
Webster
F X
FX
D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010675:Pheromones / Q000138:chemical synthesis*; D011422:Propionates / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D014631:Valerates / Q000138:chemical synthesis*
D007659:Ketones; D010675:Pheromones; D011422:Propionates; D011753:Pyrones; D014631:Valerates; C101374:stegobinone; C101373:sitophilate; C101375:sitophilure; C101372:serricornin