Beilstein J. Org. Chem.2013,9, 2762–2766, doi:10.3762/bjoc.9.310
Abstract The total synthesis of the endogenous inflammation resolving eicosanoid resolvinD2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11
. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial reduction and ester hydrolysis then gave resolvinD2 (1).
Keywords: catalysis; eicosanoid; natural product
; resolvinD2; Sonogashira coupling; total synthesis; Wittig reaction; Introduction
The resolution of inflammation is a tightly governed active process effectively mediated by a range of bioactive polyunsaturated fatty acids, peptides and proteins. In 2002, a new family of endogenously generated lipid
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Graphical Abstract
Figure 1:
Structures of resolvins D1 (1) and D2 (2).