Premium
Total Synthesis and Bioactivities of Two Proposed Structures of Maresin
Author(s) -
Sasaki Kenji,
Urabe Daisuke,
Arai Hiroyuki,
Arita Makoto,
Inoue Masayuki
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000494
Subject(s) - alkyne , enantioselective synthesis , chemistry , total synthesis , stereochemistry , aldehyde , epoxide , biochemistry , catalysis
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 BF 3 ‐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.