Yunhai Tao, Xiaomei Yang, Yi Jin
Jan 1, 2013
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0
Influential Citations
9
Citations
Journal
Synthetic Communications
Abstract
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. GRAPHICAL ABSTRACT