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Asymmetric aldol condensation as a route to polypropionate derived pheromones
1Department of Chemistry, SUNY College of Environmental Science and Forestry, Syracuse, NY 13210, USA.
Bioorganic & Medicinal Chemistry
|March 1, 1996
Abstract:
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).