Stereodefined synthesis of the four possible stereoisomers of 5,18-diHETE |
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Authors: | Yuta Suganuma Shuhei Tanabe Yusuke Sugihara Yuichi Kobayashi |
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Institution: | Department of Bioengineering, Tokyo Institute of Technology, Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan |
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Abstract: | Because of the structural similarity between 5,18-diHETE and anti-inflammatory resolvin E2, synthesis of 5,18-diHETE was studied. Methyl (R)-3-hydroxyvalerate was converted to the (R)-C9–C20 phosphonium salt via alkylation of the derived iodide with propargyl alcohol dianion and subsequent Castro-Stephens coupling. The (S)-enantiomer was prepared via Mitsunobu inversion. The (R)- and (S)-enantiomers of the γ-TMS-propargylic alcohol corresponding to the C1–C7 part were constructed by asymmetric hydrogen transfer reaction and converted to the (R)- and (S)-enals by adding the aldehyde carbon using the reaction of the derived TMS-epoxide with Et2AlCN followed by hydride reduction. The (R)-enantiomer of the C1–C8 enal was coupled with the (R)-C9–C20 phosphonium salt by Wittig reaction, and the functional group in the product was transformed to afford 5R,18R-diHETE stereoselectively. Other stereoisomers were synthesized as well. |
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Keywords: | EPA metabolite Wittig olefination Castro-Stephens coupling Asymmetric hydrogen transfer Corresponding author |
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