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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 3
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Original Articles

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

, , &
Pages 415-424 | Received 29 Jan 2011, Published online: 02 Nov 2012
 

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

ACKNOWLEDGMENT

We gratefully acknowledge the State Key Laboratory of Elemento-organic Chemistry, Nankai University (Grant No. 0703), for financial support.

Notes

a Pd(OAc)2 (1 mmol), halides (0.6 mol), and electron-deficient alkenes (0.5 mol), solvent (120 mL, HOAc/H2O 5:1,v/v), <15 °C.

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