Synthesis of Tetradecapentaenoic Acid Derivatives


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Abstract

A 12-stage method for the stereoselective synthesis of tetradecapentaenoic acid derivatives using phosphoric reagents was developed. The key step in the synthesis is the Z-selective Wittig reaction between sorbaldehyde and triphenylphosphonium (6-methoxycarbonyl)hexanilide, as well as the Ramirez-Corey-Fuchs reaction and the Trost-Kazmaier rearrangement. The synthesized (2E,4E,8Z,10E,12E)-N-isobutyltetradeca-2,4,8,10,12-pentaenamide corresponds to a natural compound called γ-Sanshoöl.

About the authors

A. O. Kolodyazhnaya

V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Email: olegkol321@gmail.com
Ukraine, ul. Murmanskaya 1, Kiev, 02094

O. I. Kolodyazhny

V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Author for correspondence.
Email: olegkol321@gmail.com
Ukraine, ul. Murmanskaya 1, Kiev, 02094


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