Ultrasound assisted synthesis of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane--the sex pheromones of Leucoptera coffeella.
Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps).
Doan
Nhuan Ngoc
NN
Department of Science, Systems and Models, Roskilde University, P. O. Box 260, DK-4000 Roskilde, Denmark. dnnhuan@hcmuns.edu.vn
Le
Thach Ngoc
TN
Nguyen
Hao Cong
HC
Hansen
Poul Erik
PE
Duus
Fritz
F
D000080462:Acyclic Monoterpenes; D000473:Alkanes / Q000138:chemical synthesis*; D000818:Animals; D039821:Monoterpenes / Q000737:chemistry; D009036:Moths / Q000378:metabolism*; D012724:Sex Attractants / Q000138:chemical synthesis*; D014465:Ultrasonics
C524613:5,9-dimethylhexadecane; C421187:5,9-dimethylpentadecane; D000080462:Acyclic Monoterpenes; D000473:Alkanes; D039821:Monoterpenes; D012724:Sex Attractants; C007078:citronellol