Synthesis of the (17R)- and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm.
Both the (17R)- and (17S)-isomers of volicitin, which is contained in the oral secretion of the beet armyworm and induces corn seedlings to emit a blend of volatile compounds to attract the natural enemy of the herbivore, were synthesized via the semi-hydrogenation of an intermediary diyne and (Z)-selective olefination as the key steps. They were both obtained as crystalline compounds.
Itoh
Seiji
S
Laboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University, Inashiki-gun, Japan.
Kuwahara
Shigefumi
S
Hasegawa
Morifumi
M
Kodama
Osamu
O
D000818:Animals; D002849:Chromatography, Gas; D005973:Glutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D018411:Spodoptera / Q000737:chemistry*; D013237:Stereoisomerism; D003313:Zea mays / Q000187:drug effects / Q000378:metabolism*; D017962:alpha-Linolenic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; C419781:volicitin; D017962:alpha-Linolenic Acid; D005973:Glutamine