Synthesis of maresin 1 and (7S)-isomer

Synthesis of maresin 1 and (7S)-isomer

[Display omitted] 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...

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Veröffentlicht in:Tetrahedron letters 2014-04, Vol.55 (16), p.2738-2741
Hauptverfasser: Ogawa, Narihito, Tojo, Toshifumi, Kobayashi, Yuichi
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetry
Carbon
Docosahexaenoic acid
Epoxidation
Iodides
Joining
Ketones
Lipid mediator
Maresin 1
Stereoselective synthesis
Suzuki–Miyaura coupling
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.03.065