Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin.

Autor:	Li J; School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia., Leong MM; School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia., Stewart A; Department of Pharmacology and Therapeutics, The University of Melbourne, Parkville, Victoria, 3010, Australia., Rizzacasa MA; School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia.
Jazyk:	angličtina
Zdroj:	Beilstein journal of organic chemistry [Beilstein J Org Chem] 2013 Dec 03; Vol. 9, pp. 2762-6. Date of Electronic Publication: 2013 Dec 03 (Print Publication: 2013).
DOI:	10.3762/bjoc.9.310
Abstrakt:	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).
Databáze:	MEDLINE
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