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Synlett 1991; 1991(12): 895-897
DOI: 10.1055/s-1991-20914
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Reactivity of Tricarbonyl(pentadienyl)iron Cations: Application to the Synthesis of 5-HETE Methyl Ester

William A. Donaldson* , Chunlin Tao
  • *Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233, USA
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Publikationsdatum:
07. März 2002 (online)

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The synthesis of (5S,6E,8Z,11Z,14Z)-5-hydroxy-6,8,11, 14-icosatetraenoic acid (5-HETE) methyl ester, from tricarbonyl-(1-methoxycarbonylpentadienylium)iron hexafluorophosphate and 1-lithio-1,4-decadiyne, in 11 steps is reported. The stereochemistry of the 6,8-diene portion of the molecule (E,Z) and of the C5 alcohol functionality are controlled by use of the iron(tricarbonyl) adjunct.