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Expedient synthesis of quadrilure antipodes, the pheromone of square-necked grain beetle

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
2
Identifiers
DOI: 10.1016/0957-4166(95)00031-j
Disciplines
  • Chemistry
  • Mathematics

Abstract

Abstract Both the enantiomers of the title pheromone, ( E)-3-methyl-7-acetoxynon-3-ene ( I) have been synthesized in high enantiomeric excess via a stereoselective route. Thus, easily accessible, 3-methylpent-1-en-3-ol ( 2) was converted via a Claisen orthoester rearrangement to the ester ( 3) with exclusive ( E)-geometry. Its derivatization to the aldehyde ( 5) followed by reaction with ethylmagnesium bromide gave the racemic pheromone alcohol ( 6) in 27.7% overall yield. Its enantioselective lipase catalyzed trans-esterification directly afforded (R)- I , while its antipode was obtained from the resolved alcohol by chemical acetylation.

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