Beilstein J. Org. Chem.2013,9, 2762–2766, doi:10.3762/bjoc.9.310
Abstract The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (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 resolvin D2 (1).
Keywords: catalysis; eicosanoid; natural product
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Graphical Abstract
Figure 1:
Structures of resolvins D1 (1) and D2 (2).
Beilstein J. Org. Chem.2012,8, 283–289, doi:10.3762/bjoc.8.30
oxylipins. Common products are 7,8-dihydroxyeicosatetraenoic acid and a novel eicosanoid with an unusual γ-lactone moiety. Several prostaglandins were predominantly formed by the invasive species. The role of some of these metabolites was investigated by surveying the attachment of E. peruviana on
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Graphical Abstract
Figure 1:
UPLC–ESIMS-based metabolic profiles of Gracilaria vermiculophylla (A) and Gracilaria chilensis (B) ...