- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLVI. SYNTHESIS OF (4S,8S)-4,8-DIMETHYLDECANAL AND ITS DIMETHYL ACETAL
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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.
- Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Sul'tanmuratova, V. R.,Tolsikov, G. A.
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p. 915 - 918
(2007/10/02)
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- Pheromone Synthesis, CXXX. Synthesis of (4S,8S)- and (4S,8R)-4,8-Dimethyldecanal, the Stereoisomers of the Aggregation Pheromone of Tribolium castaneum
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(4S,8S)- and (4S,8R)-4,8-Dimethyldecanal (1) were synthesized by starting from (R)-citronellic acid (2a), methyl (S)-3-hydroxyy-2-methylpropanoate (3a), and (S)-2-methyl-1-butanol (4a).
- Mori, Kenji,Takikawa, Hirosato
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p. 497 - 500
(2007/10/02)
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- DIASTEREOTOPIC GROUP SELECTIVITY AT A PROSTEREOGENIC CARBON CENTER: SYNTHESIS OF (+/-)-SYN-4,8-DIMETHYLDECANAL
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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
- Schreiber, Stuart L.,Hulin, Bernard
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p. 4561 - 4564
(2007/10/02)
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- Synthesis of 4(RS),8(S)-Dimethyldecanal: An Aggrigation Pheromone of Red Flour Beetles
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A simple and straight forward synthesis of the pheromone 4(RS),8(S)-dimethyldecanal (IX) has been described starting from 7-hydroxycitronellal (I).
- Randad, R. S.,Kulkarni, G. H.
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p. 296 - 298
(2007/10/02)
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- SYNTHESIS OF ALL OF THE FOUR POSSIBLE STEREOISOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF THE FLOUR BEETLES
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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.
- Mori, Kenji,Kuwahara, Shigefumi,Ueda, Hiraki
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p. 2439 - 2444
(2007/10/02)
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