Total synthesis and bioactivities of two proposed structures of maresin

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

doi:10.1002/asia.201000494

Total synthesis and bioactivities of two proposed structures of maresin

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

Research output: Contribution to journal › Article › peer-review

37 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 language	English
Pages (from-to)	534-543
Number of pages	10
Journal	Chemistry - An Asian Journal
Volume	6
Issue number	2
DOIs	https://doi.org/10.1002/asia.201000494
Publication status	Published - 2011 Feb 1
Externally published	Yes

Keywords

biological activity
fatty acids
inflammation
olefination
total synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.201000494

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AU - Sasaki, Kenji

AU - Urabe, Daisuke

AU - Arai, Hiroyuki

AU - Arita, Makoto

AU - Inoue, Masayuki

PY - 2011/2/1

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AB - 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.

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KW - fatty acids

KW - inflammation

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KW - total synthesis

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Total synthesis and bioactivities of two proposed structures of maresin

Abstract

Keywords

ASJC Scopus subject areas

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