Enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri

Mini‐review: recent advances in the identification and application of sex pheromones of gall midges (Diptera: Cecidomyiidae)

“…10 In the field, the racemate of the stereoisomer (2S,12R,8Z)-2,12-diacetoxy-8-heptadecene was attractive to male blackcurrant leaf midges, whereas the racemate of the major component (2R,13R,8Z)-2,13-diacetoxy-8-heptadecenene of pear leaf midge (Dasineura pyri) was not. 17 Dasineura oxycoccana on cranberry and blueberry responded to different sex pheromones. Ovipositor extracts from cranberry tipworm females contained one component (8Z)-2,14-diacetoxy-8heptadecene that elicited antennal responses from the males.…”

“…Analysis of gland extracts of the female blackcurrant leaf midge ( Dasineura tetensi ) identified the major compound as (8 Z )‐2,12‐diacetoxy‐8‐heptadecene 10 . In the field, the racemate of the stereoisomer (2 S ,12 R ,8 Z )‐2,12‐diacetoxy‐8‐heptadecene was attractive to male blackcurrant leaf midges, whereas the racemate of the major component (2 R ,13 R ,8 Z )‐2,13‐diacetoxy‐8‐heptadecenene of pear leaf midge ( Dasineura pyri ) was not 17 …”

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

“…): 42 , 47 Plutella xylostella (Lep., Plutellidae): 43 , 48 Trichoplusia ni (Lep., Noctuidae): 44 , 49 Tortrix viridana (Lep., Tortricidae): 45 , 50 Grapholita molesta , G. funebrana , and Hedya nubiferana (Lep., Tortricidae): ( E )- and ( Z )- 46 , 51 Plutella xylostella (Lep., Plutellidae): 47 , 52 moth (Lep.) 48–52 , 47 Keiferia lycopersicella (Lep., Gelechiidae): 53 , 53 Anthistarcha binocularis (Lep., Gelechiidae): 54 and 55 , 54 Illiberis pruni (Lep., Zygaenidae): 56 and 57 , 55 Rhyacionia buoliana (Lep., Tortricidae): 58 , 50 Phyllonorycter blancardella (Lep., Gracillariidae): ( Z )- 59 , 56 Ostrinia furnacalis (Lep., Crambidae): ( E )- and ( Z )- 60 , 57 Melanotus communis (Col., Elateridae): 61 , 58 Dasineura pyri (Dip., Cecidomyiidae): 62 , 59 Ithomia salapia (Lep., Nymphalidae): 63 and 64 , 60 Cydia pomonella (Lep., Tortricidae): 65 , 61,62 Stathmopoda masinissa (Lep., Stathmopodidae): 66 and 67 , 63 Lobesia botrana (Lep., Tortricidae): 68 , 64–66 Malacosoma neustria and Dendrolimus punctatus (Lep., Lasiocampidae): 69 , Spodoptera littoralis and S. litura (Lep., Noctuidae): 70 , 67 Thaumetopoea bonjeani (Lep., Notodontidae): 71 and 72 , 68 Acanthoscelides obtectus (Col., Chrysomelidae): 73 , 69 Plodia interpunctella hb. (Lep., Pyralidae): 74 , 70 Pectinophora gossypiella (Lep., Gelechiidae): 75 , 29,71 Spodoptera exigua (Lep., Noctuidae): 76 , 72 Phyllonorycter ringoniella (Lep., Gracillariidae): 77 , 73,74 Loepa sakaei (Lep., Saturniinae): 78 , 75 Symmetrischema tangolias (Lep., Gelechiidae): 79 , 76 Tuta absoluta (Lep., Gelechiidae):…”