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Bioscience, Biotechnology, and Biochemistry Volume 69, 2005 - Issue 12
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Original Articles

Synthesis of the Four Stereoisomers of 2,6-Dimethyloctane-1,8-dioic Acid, a Component of the Copulation Release Pheromone of the Cowpea Weevil, Callosobruchus maculatus

Tomonori NAKAIDepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
,
Arata YAJIMADepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
,
Kazuaki AKASAKAGraduate School of Life Science, Tohoku University
,
Takayuki KAIHOKUDepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
,
Miki OHTAKIDepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
,
Tomoo NUKADADepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
,
Hiroshi OHRUIGraduate School of Life Science, Tohoku University
&
Goro YABUTADepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture
 show all
Pages 2401-2408 | Received 20 Jul 2005, Accepted 22 Aug 2005, Published online: 22 May 2014

Citations (19)

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Arata YAJIMA. (2011) Synthesis of Microbial Signaling Molecules and Their Stereochemistry-Activity Relationships. Bioscience, Biotechnology, and Biochemistry 75:8, pages 1418-1429.
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Articles from other publishers (18)

Christian P. Bold, Kay YeungFelix PapeDaniel Kaiser & Varinder K. Aggarwal. (2022) Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F. Organic Letters 24:51, pages 9398-9402.
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Kazuaki Akasaka. (2022) A Highly Selective and Sensitive Chiral Derivatization Method for High- Performance Liquid Chromatographic Determination of the Stereoisomer Composition of Natural Products With Chiral Branched Alkyl Chains. Journal of Chemical Ecology 48:5-6, pages 554-568.
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Wen-Jun Wei, Su-Bei Tan, Tao Guo, Ya Wang & Jun Chang. (2021) Chemical Constituents of the Fresh Rhizome of Zingiber officinale. Chemistry of Natural Compounds 57:5, pages 968-969.
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Shaimaa Awadain Elsharif & Andrea Buettner. (2016) Structure–Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives. Journal of Agricultural and Food Chemistry 66:10, pages 2324-2333.
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Jiang Liu, Seikou Nakamura, Bin Xu, Takahiro Matsumoto, Tomoe Ohta, Katsuyoshi Fujimoto, Keiko Ogawa, Masashi Fukaya, Shiori Miyake, Masayuki Yoshikawa & Hisashi Matsuda. (2014) Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus. Journal of Natural Medicines 69:1, pages 135-141.
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Anna M Bogazkaya, Clemens J von Bühler, Sebastian Kriening, Alexandrine Busch, Alexander Seifert, Jürgen Pleiss, Sabine Laschat & Vlada B Urlacher. (2014) Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX . Beilstein Journal of Organic Chemistry 10, pages 1347-1353.
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Alexander P. Pulis, Philipp Fackler & Varinder K. Aggarwal. (2014) Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone α1 Using Lithiation/Borylation Reactions . Angewandte Chemie International Edition 53:17, pages 4382-4385.
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Alexander P. Pulis, Philipp Fackler & Varinder K. Aggarwal. (2014) Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone α1 Using Lithiation/Borylation Reactions . Angewandte Chemie 126:17, pages 4471-4474.
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Catalina Ferrer, Peter Fodran, Santiago Barroso, Robert Gibson, Ellen C. Hopmans, Jaap Sinninghe Damsté, Stefan Schouten & Adriaan J. Minnaard. (2013) Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol. Organic & Biomolecular Chemistry 11:15, pages 2482.
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Johannes F. Teichert, Tim den Hartog, Miriam Hanstein, Christian Smit, Bjorn ter Horst, Victor Hernandez-Olmos, Ben L. Feringa & Adriaan J. Minnaard. (2011) Organocatalytic Reduction of Carbon−Carbon Double Bonds in Racemization-Sensitive Compounds. ACS Catalysis 1:4, pages 309-315.
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Kenji Shimomura, Kazuaki Akasaka, Arata Yajima, Takanori Mimura, Shunsuke Yajima & Kanju Ohsawa. (2010) Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.). Journal of Chemical Ecology 36:9, pages 955-965.
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Christian Smit, Marco W. Fraaije & Adriaan J. Minnaard. (2008) Reduction of Carbon−Carbon Double Bonds Using Organocatalytically Generated Diimide. The Journal of Organic Chemistry 73:23, pages 9482-9485.
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Arata Yajima, Yong Qin, Xuan Zhou, Naoki Kawanishi, Xue Xiao, Jue Wang, Dan Zhang, Yi Wu, Tomoo Nukada, Goro Yabuta, Jianhua Qi, Tomoyo Asano & Youji Sakagami. (2008) Synthesis and absolute configuration of hormone α1. Nature Chemical Biology 4:4, pages 235-237.
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Hiroshi Ohrui. (2008) Development of Highly Potent Chiral Discrimination Methods That Solve the Problems of Diastereomer Method. Analytical Sciences 24:1, pages 31-38.
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Arata Yajima, Kazuaki Akasaka, Masamichi Yamamoto, Sachiko Ohmori, Tomoo Nukada & Goro Yabuta. (2007) Direct Determination of the Stereoisomeric Composition of Callosobruchusic Acid, the Copulation Release Pheromone of the Azuki Bean Weevil, Callosobruchus chinensis L., by the 2D-Ohrui-Akasaka Method. Journal of Chemical Ecology 33:7.
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Satoshi Nojima, Kenji Shimomura, Hiroshi Honda, Izuru Yamamoto & Kanju Ohsawa. (2007) Contact Sex Pheromone Components of the Cowpea Weevil, Callosobruchus maculatus. Journal of Chemical Ecology 33:5, pages 923-933.
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Hiroshi OHRUI. (2007) Development of highly potent chiral discrimination methods that solve the problems of the diastereomer method. Proceedings of the Japan Academy, Series B 83:5, pages 127-135.
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Arata Yajima, Kazuaki Akasaka, Tomonori Nakai, Hiroki Maehara, Tomoo Nukada, Hiroshi Ohrui & Goro Yabuta. (2006) Direct determination of the stereoisomer constitution by 2D-HPLC and stereochemistry–pheromone activity relationship of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus. Tetrahedron 62:18, pages 4590-4596.
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