Simple synthesis of 5,9-dimethylated long-chain alkanes, the sex pheromones of leaf miner moths.
Each stereoisomeric mixture of 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and the minor sex pheromone components of Perileucoptera coffeella, respectively, was synthesized in about 25% overall yield through 6 steps from beta-citronellol. 5,9-Dimethylheptadecane, the major sex pheromone component of Leucoptera malifoliella, was also synthesized analogously as a stereoisomeric mixture in a 22% overall yield.
Liang
T
T
Laboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University, Japan.
Kuwahara
S
S
Hasegawa
M
M
Kodama
O
O
D000080462:Acyclic Monoterpenes; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D039821:Monoterpenes; D009036:Moths / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry
C421188:5,9-dimethylheptadecane; C421187:5,9-dimethylpentadecane; D000080462:Acyclic Monoterpenes; D000473:Alkanes; D039821:Monoterpenes; D012724:Sex Attractants; D013729:Terpenes; C007078:citronellol