title: Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity.
abstract: The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.
authors.affiliation: Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada.
authors.forename: A C
authors.initials: AC
authors.lastname: Oehlschlager
authors.forename: G G
authors.initials: GG
authors.lastname: King
authors.forename: H D
authors.initials: HD
authors.lastname: Pierce
authors.forename: A M
authors.initials: AM
authors.lastname: Pierce
authors.forename: K N
authors.initials: KN
authors.lastname: Slessor
authors.forename: J G
authors.initials: JG
authors.lastname: Millar
authors.forename: J H
authors.initials: JH
authors.lastname: Borden