286367-55-3Relevant academic research and scientific papers
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
Ivanov, Igor V.,Groza, Nataliya V.,Romanov, Stepan G.,Kühn, Hartmut,Myagkova, Galina I.
, p. 691 - 694 (2000)
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%.
