1268720-28-0Relevant articles and documents
Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1
Rodriguez, Ana R.,Spur, Bernd W.
, p. 4169 - 4172 (2012)
The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd0/CuI Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.
Total synthesis and bioactivities of two proposed structures of maresin
Sasaki, Kenji,Urabe, Daisuke,Arai, Hiroyuki,Arita, Makoto,Inoue, Masayuki
, p. 534 - 543 (2011/10/12)
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. Copyright
