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Synthesis 1993; 1993(4): 411-420
DOI: 10.1055/s-1993-25874
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A Concise, Efficient and Flexible Strategy for the Synthesis of the Pheromones of Oryzaephilus and Cryptolestes Grain Beetles

Christopher D. J. Boden* , John Chambers, Ian D. R. Stevens
  • *Department of Chemistry, The University, Highfield, Southampton SO9 5NH, England
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Publication Date:
17 September 2002 (online)

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Six of the seven macrolide components of the pheromone systems of grain beetles of the genera Oryzaephilus and Cryptolestes are synthesised by new routes of greatly improved efficiency. Iterative methodology based on the Wittig olefination is employed for the construction of the (Z,Z)-1,4-diene subunits in three of the lactones; chlorite oxidation of (Z)-3-alkenals derived by this methodology is used to form the (Z)-3-alkenoic acid functionalities present in four of the targets. The use of recently described conditions for the cyclisation of a Combretastatin analogue gives dramatically increased yields for the macrolactonisation steps in all six cases.