18607-53-9Relevant academic research and scientific papers
Metathesis-mediated synthesis of (R)-10-Methyl-2-tridecanone, the southern corn rootworm pheromone
Shikichi, Yasumasa,Moriy, Kenji
, p. 407 - 409 (2012)
(R)-10-Methyl-2-tridecanone, the female sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi Barber), was synthesized in 9 steps from methyl (S)-3-hydroxy-2-methylpropanoate in a 15.7% overall yield. Olefin cross metathesis between (R)-6-methyl-1-nonene and 5-hexen-2-one employing Grubbs' first-generation catalyst was the key step of the synthesis.
Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
, p. 111 - 121 (2007/10/03)
Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
Pheromone Synthesis, CLXVII. - Synthesis of All of the Eight Stereoisomers of Methyl 2,6,10-Trimethyltridecanoate, the Male-produced Pheromone of the Stink Bugs, Euschistus heros and E. obscurus
Mori, Kenji,Murata, Noriaki
, p. 1153 - 1160 (2007/10/02)
All of the eight possible stereoisomers of methyl 2,6,10-trimethyltridecanoate (1), the male-produced attractant pheromone of the South American soybean pest, Euschistus heros, and that of E. obscurus, are synthesized by starting from the enantiomers of citronellol (2) and methyl 3-hydroxy-2-methylpropanoate (9). - Key Words: Euschistus heros / Euschistus obscurus / Pheromones / Stink bugs / Sulfones, alkylation of / Tridecanoate, methyl 2,6,10-trimethyl-
Stereochemistry of Aliphatic Carbocations, 14. Alkyl Shifts from Secondary to Primary Carbon Atoms
Kirmse, Wolfgang,Guenther, Bernd-Rainer,Knist, Johannes,Kratz, Sigrid,Loosen, Karin,et al.
, p. 2127 - 2139 (2007/10/02)
Alkyl shifts from secondary to primary carbon atoms have been induced by the nitrous acid deamination of suitable amines (4, 22, 39, 51); they include sequential rearrangements (-CH3,CH3 and -CH3,H).Predominant although incomplete inversion at the migration origin has been observed (Me 70percent, Et 62-64percent, nPr 65percent, iPr 64percent, tBu 55percent).Our results require the intervention of open secondary carbocations which may be preceded by less stable bridged intermediates.
