Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer

References

• Ando T, Inomata S, Yamamoto M. Lepidopteran sex pheromones. Top. Curr. Chem. 2004;239:51–96.10.1007/b96138
   PubMed Web of Science ®Google Scholar
• Ando T. Internet database 2013 [Internet]. Available from: http://www.tuat.ac.jp/~antetsu/LepiPheroList.htm
   Google Scholar
• El-Sayed AM. Internet database 2013 [Internet]. Available from: http://www.pherobase.com/
   Google Scholar
• Bierl BA, Beroza M, Collier CW. Potent sex attractant of the gypsy moth: its isolation, identification, and synthesis. Science. 1970;170:87–89.10.1126/science.170.3953.87
   PubMed Web of Science ®Google Scholar
• Yamamoto M, Kamata T, Do ND, Adachi Y, Kinjo M, Ando T. A novel lepidopteran sex pheromone produced by females of a lithosiinae species, Lyclene dharma dharma, in the family of Arctiidae. Biosci. Biotechnol. Biochem. 2007;71:2860–2863.10.1271/bbb.70551
   PubMed Web of Science ®Google Scholar
• Gries R, Gries G, King GGS, Maier CT. Sex pheromone components of the apple leafminer, Lyonetia prunifoliella. J. Chem. Ecol. 1997;23:1119–1130.10.1023/B:JOEC.0000006390.43868.3b
   Web of Science ®Google Scholar
• Park JH, Han KS, Mori K, Boo KS. Right stereoisomers for sex pheromone components of the apple leafminer, Lyonetia prunifoliella, in Korea. J. Chem. Ecol. 2002;28:2515–2525.10.1023/A:1021488103491
   PubMed Web of Science ®Google Scholar
• Sekita N, Yamada M. Life history of Lyonetia prunifoliella Hübner subsp. malinella (Matsumura) (Lepidoptera: Lyonetiidae). Appl. Entomol. Zool. 1979;14:285–292.
   Web of Science ®Google Scholar
• Tamagawa H, Takikawa H, Mori K. Pheromone synthesis, CXCII. Synthesis of all the stereoisomers of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane and 5,9-dimethylheptadecane, the sex pheromone components of the apple leafminer, Lyonetia prunifoliella. Eur. J. Org. Chem. 1999;1999:973–978.10.1002/(ISSN)1099-0690
   Google Scholar
• Nakamura Y, Mori K. Pheromone synthesis, CCIV. Synthesis of the enantiomers of anti-2,6-dimethylphentane-1,7-diol monotetrahydropyranyl ether and their conversion into the enantiomers of the sex pheromone components of the apple leafminer, Lyonetia prunifoliella. Eur. J. Org. Chem. 2000;2000:2745–2753.10.1002/(ISSN)1099-0690
   Google Scholar
• van Summeren RP, Reijmer SJW, Feringa BL, Minnaard AJ. Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones. Chem. Commun. 2005;2005:1387–1389.10.1039/b419268k
   Web of Science ®Google Scholar
• Yadav JS, Gayathri KU, Thrimurtulu N, Prasad AR. Stereoselective synthesis of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane, and 5,9-dimethylheptadecane, the sex pheromones of female apple leafminer. Tetrahedron. 2009;65:3536–3544.10.1016/j.tet.2009.01.093
   Web of Science ®Google Scholar
• Taguri T, Yamakawa R, Fujii T, Muraki Y, Ando T. Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones. Tetrahedron: Asymmetry. 2012;23:852–858.10.1016/j.tetasy.2012.05.023
   Web of Science ®Google Scholar
• Krapcho AP, Weimaster JF, Eldridge JM, Jahngen EGE Jr, Lovey AJ, Stephens WP. Synthetic applications and mechanism studies of the decarbalkoxylations of geminal diesters and related systems effected in Me2SO by water and/or by water with added salts. J. Org. Chem. 1978;43:138–147.10.1021/jo00395a032
   Web of Science ®Google Scholar
• Muraki Y, Taguri T, Yamamoto M, Zarbin PHG, Ando T. Synthesis of all four stereoisomers of 6,10,13-trimethyltetradecan-2-one, a sex pheromone component produced by males of the stink bug Pallantia macunaima. Eur. J. Org. Chem. 2013;2013:2209–2215.10.1002/ejoc.201201688
   Web of Science ®Google Scholar
• Fávaro CF, Soldi RA, Ando T, Aldrich JR, Zarbin PH. (6R,10S)-Pallantione: the first ketone identified as sex pheromone in stink bugs. Org. Lett. 2013;15:1822–1825.10.1021/ol400413w
   PubMed Web of Science ®Google Scholar
• Taguri T, Yamamoto M, Fujii T, Muraki Y, Ando T. Synthesis of four stereoisomers of (S)-2-methylpent-3-yl 3,13-dimethylpentadecanoate, a sex pheromone of the bagworm moth clania variegate, using stereospecific inversion of secondary sulfonates as a key step. Eur. J. Org. Chem. 2013;2013:6924–6933.10.1002/ejoc.v2013.30
   Google Scholar