92935-19-8Relevant academic research and scientific papers
Syntheses of the Sex-Attractant of Pine Sawfies
Kikukawa, Tadashi,Imaida, Motomasa,Tai, Akira
, p. 1954 - 1960 (1984)
In order to establish the stereochemistry of the sex attractant of various species of pine sawflies, (2S,3R,7R)-, (2S,3R,7S)- and (2S,3S,7S)-2-acetoxy- and 2-propionyloxy-3,7-dimethylpentadecane were synthesized.The alcohol moiety of each pheromone was prepared by the coupling of Grignard reagent of C12 block with tosylate of C5 block.The C12 block, (R)- and (S)-1-bromo-2-methylundecane, were prepared from (R)-(+)-pulegone.The C5 block, (2R,3S)- or (2S,3S)-2-methyl-3-tetrahydropyranyloxy-1-(tosyloxy)butane, were derived from (2S,3S)- or (2R,3S)-2-methyl-3-hydroxy butyric acid prepared by the enantio-differentiating hydrogenation of methyl 2-methyl-3-oxobutyrate over the asymmetrically modified nickel catalyst.
A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate and propionate, the sex pheromones of pine sawflies
Huang, Pei-Qiang,Lan, Hong-Qiao,Zheng, Xiao,Ruan, Yuan-Ping
, p. 3964 - 3967 (2007/10/03)
(2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction-epoxide formation-reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.
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.
Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates
Tai, Akira,Higashiura, Yasutomo,Kakizaki, Masashi,Naito, Tikahiko,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Hara, Hideho,Hayashi, Naotaka
, p. 607 - 608 (2007/10/03)
(1S, 2R, 6RS)-1,2,6-Trimethyldecyl propionate, a lower homolog of the sex pheromone of known sawflies, strongly attracted Diprion nipponica, a popular species in Japan.
Preparation of Stereochemically Pure Sex Pheromone Components of the Pine Sawfly (Neodiprion sertifer) and Field Tests of the Synthetic Compounds
Tai, Akira,Morimoto, Naotake,Yoshikawa, Masato,Uehara, Kazuya,Sugimura, Takashi,Kikukawa, Tadashi
, p. 1753 - 1762 (2007/10/02)
Stereochemically pure pheromone components of the pine sawfly, acetates of (2S,3S,7S)- and (2S,3R,7R)-3,7-dimethylpentadecan-2-ol, were prepared by an improved synthetic procedure.Mixtures of the newly prepared compounds were tested in the field (red pine forests in Hyogo and Nagano, Japan) for their attraction of Neodiprion sertifer.The maximum response was observed in mixtures of the ratio (2S,3R,7R)/(2S,3S,7S)-10-3: 1 to 10-4: 1.When the results are compared with those in Michigan, U.S.A., N. sertifer in Japan responded less specifically to certain blending ratios of diastereomers than in America.
