Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer Diatraea saccharalis.
Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.
Santangelo
Ellen M
EM
Department of Chemistry, Organic Chemistry, The Royal Institute of Technology, SE-10044 Stockholm, Sweden.
Coracini
Myrian
M
Witzgall
Peter
P
Correa
Arlene G
AG
Unelius
C Rikard
CR
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001938:Brazil; D005260:Female; D007915:Lepidoptera / Q000737:chemistry*; D013058:Mass Spectrometry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000466:Alkadienes; D010675:Pheromones