Abstract
The sex pheromone of Sitodiplosis mosellana, (2 S,7 S)-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 (2 S,7 S)-nonanediol with a diastereoisomeric excess of 94% as measured by gas chromatographic analysis of the diacetylated product.
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