Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5276351 | Tetrahedron Letters | 2007 | 4 Pages |
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.
Graphical abstractThe sex pheromone of the orange wheat blossom midge is synthesised by RCM from a sterically hindered silaketal with a de of 94%.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Antony M. Hooper, Samuel Dufour, Sophie Willaert, Sophie Pouvreau, John A. Pickett,