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Synthesis 2000; 2000(5): 691-694
DOI: 10.1055/s-2000-6400
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Total Synthesis of the Lipoxygenase Substrates (5Z,8Z,11Z,14Z)-Nonadeca-5,8,11,14-tetraene-1,19-dioic Acid and (5Z,8Z,11Z,14Z)-20,20-Dimethylheneicosa-5,8,11,14-tetraenoic Acid

Igor V. Ivanov* , Nataliya V. Groza, Stepan G. Romanov, Hartmut Kühn, Galina I. Myagkova
  • *M. V. Lomonosov State Academy of Fine Chemical Technology, 117571 Moscow, Russian Federation; Fax + 7 09 54 35 87 11
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Publication Date:
31 December 2000 (online)

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For mechanistic studies on the lipoxygenase reaction, the special substrate fatty acids (5Z,8Z,11Z,14Z)-nonadeca-5,8,11,14-tetraene-1,19-dioic and (5Z,8Z,11Z,14Z)-20,20-dimethylheneicosa-5,8,11,14-tetraenoic acids were synthesized. The synthetic scheme involves a joint route for the formation of (5Z,8Z,11Z,14Z)-nonadeca-5,8,11,14-tetraene-1,19-dioic acid, which is based on the polyacetylenic approach. Regioselective reduction of the ω-carboxylic group to the primary alcohol, exchange of an OH-group to corresponding iodine and subsequent coupling with low-order organocuprates (t-Bu2CuLi) resulted in the formation of (5Z,8Z,11Z,14Z)-20,20-dimethylheneicosa-5,8,11,14-tetraenoic acid with an overall yield of 11%.

polyunsaturated fatty acids - cross-coupling reaction - copper(I) catalysis - Gilman cuprates - lipoxygenase

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