87106-39-6Relevant articles and documents
OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLVI. SYNTHESIS OF (4S,8S)-4,8-DIMETHYLDECANAL AND ITS DIMETHYL ACETAL
Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Sul'tanmuratova, V. R.,Tolsikov, G. A.
, p. 915 - 918 (2007/10/02)
From accessible chiral structural blocks, namely, (R)-methyl-citronellate and (S)-2-methyl-1-butanol, (6S,10S)-2,6,10-trimethyl-2-dodecene was synthesized.The ozonolysis of this gave (4S,8S)-4,8-dimethyldecanal, one of the stereoisomers of the aggregation pheromone of the meal worms Tribolium confusium and T. castaneum, and its dimethyl acetal.
DIASTEREOTOPIC GROUP SELECTIVITY AT A PROSTEREOGENIC CARBON CENTER: SYNTHESIS OF (+/-)-SYN-4,8-DIMETHYLDECANAL
Schreiber, Stuart L.,Hulin, Bernard
, p. 4561 - 4564 (2007/10/02)
A group selective dealkylation reaction of a bridged ketal with trimethylsilyl iodide serves to control stereochemistry at carbon centers that are separated by five atoms.In combination with the iron/copper promoted fragmentation reaction of a hydroperoxi
SYNTHESIS OF ALL OF THE FOUR POSSIBLE STEREOISOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF THE FLOUR BEETLES
Mori, Kenji,Kuwahara, Shigefumi,Ueda, Hiraki
, p. 2439 - 2444 (2007/10/02)
The four stereoisomers of 4,8-dimethyldecanal were synthesized employing organometallic or electrolytic coupling reactions as the key step.The response of the red flour beetle, Tribolium castaneum, to the (4R,8R)-isomer was identical with that to the natural pheromone, while other isomers induced only very weak or no responses.The (4R,8R)-isomer is therefore the natural pheromone.