Synthesis of (2S,7S)-dibutyroxynonane, the sex pheromone of the orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae), by diastereoselective silicon-tethered ring-closing metathesis |
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Authors: | Antony M. Hooper |
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Affiliation: | Biological Chemistry Department, Rothamsted Research, Harpenden, Herts AL5 2JQ, UK |
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Abstract: | The sex pheromone of Sitodiplosis mosellana, (2S,7S)-dibutyroxynonane, has been synthesised using a mixed di-t-butylsilaketal prepared from (S)-5-hexen-2-ol and prochiral 1,4-pentadiene-3-ol. Ring-closing metathesis occurs diastereoselectively and after the removal of the silyl group and the reduction of the double bonds, generates (2S,7S)-nonanediol with a diastereoisomeric excess of 94% as measured by gas chromatographic analysis of the diacetylated product. |
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Keywords: | Sitodiplosis mosellana Orange wheat blossom midge Sex pheromone Ring-closing metathesis Silicon-tethered Diastereoselective |
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