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Synthesis 1989; 1989(12): 936-938
DOI: 10.1055/s-1989-27435
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Synthesis of 7,11-Dienes from Enol Ether and Grignard Reagents Under Nickel Catalysis: Sex Pheromones of Drosophila Melanogaster

Terry L. Davis* , David A. Carlson
  • *Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
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Publication Date:
02 May 2002 (online)

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A modified Felkin reaction was used to prepare (Z)-4-undecen-1-ol (5) from hexylmagnesium bromide (2) and an enol ether, dihydropyran (3) catalyzed by low-valent nickel species, bis(diphenylphosphino)propanenickel(II) chloride (4). Pyridinium chlorochromate oxidation followed by chromatography afforded (Z)-4-undecenal (6), which was treated with hexadecyltriphenylphosphorane (7b) to yield (Z,Z)-7,11-heptacosadiene (8b). Two homologs (Z,Z)-7,11-pentacosadiene (8a) and (Z,Z) -7,11-nonacosadiene (8c) were also synthesized.