Abstract
The first enantioselective synthesis of chichimol ketone (4-methyl-1-hepten-3-one) is described and the absolute configuration of the main semiochemical compound is determined as having an ( S)-configuration. The synthesis features the use of a ruthenium catalytic asymmetric hydrogenation reaction to introduce chirality into acid 2. The synthetic chichimol ketone ( S)- 1 displayed a specific rotation that was in accordance with that of the natural product, thereby supporting the ( S) configuration for natural chichimol ketone. To assure the correct stereochemical assignment, ( S)- 1 was converted in the known ketone ( S)- 5: the main alarm pheromone of the ant Atta texana that is 400 times more active than its ( R)-enantiomers.
Published Version
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