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

Hooper, A., Dufour, S., Willaert, S., Pouvreau, S. and Pickett, J. ORCID: https://orcid.org/0000-0002-8386-3770 2007. 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. Tetrahedron Letters 48 (34) , pp. 5991-5994. 10.1016/j.tetlet.2007.06.124

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Elsevier
ISSN:	0040-4039
Date of Acceptance:	20 June 2007
Last Modified:	18 Feb 2026 16:45
URI:	https://orca.cardiff.ac.uk/id/eprint/184984

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