Facile Synthesis of (Z,E)-9,11-Hexadecadienal,the Major Sex Pheromone Component of the Sugarcane Borer Diatraea saccharalis: An Efficient Strategy for Synthesis of (Z,E)-Dienic Pheromones |
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| Authors: | Yunhai Tao Xiaomei Yang Yi Jin Qingzhong Wang |
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| Institution: | 1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming , China;2. State Key Laboratory of Elemento-organic Chemistry , Nankai University , Tianjin , China cloudsea2000@sina.com;4. Yunnan University of Traditional Chinese Medicine , Kunming , China;5. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming , China |
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| Abstract: | Practical and improved procedures for the synthesis of 7-bromo-(Z,E)-4,6-heptadienal by Pd(II)-catalyzed coupling reaction were developed. Based on the improved method, an efficient and stereoselective synthesis of (Z,E)-9,11-hexadecadienal, the main pheromone component of the sugarcane borer, Diatraea saccharalis, was achieved in 38% overall yield, which more desirable then previously reported methods. The stereochemistry relied on cross-coupling between Grignard reagent and protected 7-bromo-(Z,E)-4,6-heptadienal. The concise and facile synthetic strategy described herein provided a generally synthetic approach to other (Z,E)-dienic compounds. |
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| Keywords: | 7-Bromo-(Z E)-4 6-heptadienal Kumada cross-coupling pheromone synthesis sugarcane borer (Z E)-9 11-hexadecadienal |
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