Total synthesis and bioactivities of two proposed structures of maresin

Kenji Sasaki, Daisuke Urabe, Hiroyuki Arai, Makoto Arita, Masayuki Inoue

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model.

Original languageEnglish
Pages (from-to)534-543
Number of pages10
JournalChemistry - An Asian Journal
Volume6
Issue number2
DOIs
Publication statusPublished - 2011 Feb 1
Externally publishedYes

Keywords

  • biological activity
  • fatty acids
  • inflammation
  • olefination
  • total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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