A Facile Synthesis of 4,8-Dimethyldecanal, Aggregation Pheromone of Flour Beetles, and Its Analogues

Synthesis of Optically Active Aggregation Pheromone Analogues of the Red Flour Beetle,Tribolium castaneum

“…on a Shimadzu GC-6A gas chromatograph equipped with an FID using glass column (3 mm x 2 m) packed with 5% SE-30 or 5% PEG-20M (both on Chromosorb WAW, 80 ro.J 100 mesh). (4). This compound was prepared by oxidation of (R)-( + )-citroneIl61 with activated.…”

An efficient asymmetric synthesis of (4R,8R)‐4,8‐dimethyldecanal, the most active component of natural Tribolure

“…The reaction was allowed to stir for another 30 min, 5 (2.0 g, 10.4 mmol) in anhydrous THF (5 mL) was added dropwise, and the resulting mixture was stirred for another 3 hr at −78 C. The reaction system was slowly warmed to −50 C and stirred for 15 hr. After completion of the reaction, the mixture was cooled to −78 C and quenched with saturated NH 4 A flask was charged with solution of 3 (1.8 g, 7.5 mmol) ethyl acetate, 5% catalyst Pt/C (95.0 mg), the atmosphere in the flask was changed to hydrogen three times. And the reaction mixture was allowed to stir at room temperature for 10 hr.…”

“…Namely, the ratio of the four stereoisomers (4R,8R)-1/ (4R,8S)-1/(4S,8R)-1/(4S,8S)-1 is 4/4/1/1. [4][5][6][7][8][9][10][11][12] Among them, the most active component is (4R,8R)-4,8-dimethyldecanal ( Figure 1), which has two chiral methyl branches and a linear carbon chain aldehyde.…”

“…[12] Suzuki reported the first synthesis and developed his synthesis after he discovered the pheromone. [4] Afterward, the first asymmetric synthesis of all four stereoisomers of 1 was achieved in 1983 through 11 steps by the distinguished Japanese insect pheromone expert, Mori. [13] And, more asymmetric syntheses of 4,8-dimethyldecanal 1 [14][15][16][17][18][19][20] using chiral starting materials can be found in the literature.…”

Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp

“…In 1980 Suzuki identified and then synthesized the aggregation pheromone common to both species of Tribolium, the 4,8-dimethyldecanal (1) 2,3 . In 1983 Mori and co-workers 4,1 established the absolute configuration of this natural pheromone as (4R, 8R), when they carried out the synthesis of all of the four possible stereoisomers of (1).…”