Total synthesis and bioactivities of two proposed structures of maresin

K Sasaki, D Urabe, H Arai, M Arita…

Index: Sasaki, Kenji; Urabe, Daisuke; Arai, Hiroyuki; Arita, Makoto; Inoue, Masayuki Chemistry - An Asian Journal, 2011 , vol. 6, # 2 p. 534 - 543

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Citation Number: 26

Abstract

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 ...