Synthesis of maresin 1 and (7S)-isomer |
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| Authors: | Narihito Ogawa Toshifumi TojoYuichi Kobayashi |
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| Affiliation: | Department of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan |
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| Abstract: | Maresin 1 (with the 7R carbon) and (7S)-maresin 1 were synthesized stereoselectively. The conjugated triene system was constructed by Pd-catalyzed coupling of the trans cis-dienylborane (the C10–C22 part) with the trans vinyl iodide corresponding to the C1–C9 part. The stereogenic centers at C7 and C14 were created by Ru-catalyzed asymmetric reduction of ketone and asymmetric epoxidation/kinetic resolution of the racemic alcohol, respectively. |
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| Keywords: | Maresin 1 Stereoselective synthesis Suzuki&ndash Miyaura coupling Lipid mediator Docosahexaenoic acid |
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