Synthesis of maresin 1 and (7S)-isomer

Narihito Ogawa, Toshifumi Tojo, Yuichi Kobayashi

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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.

Original languageEnglish
Pages (from-to)2738-2741
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number16
DOIs
Publication statusPublished - 16 Apr 2014

Keywords

  • Docosahexaenoic acid
  • Lipid mediator
  • Maresin 1
  • Stereoselective synthesis
  • Suzuki-Miyaura coupling

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