title: Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin.
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).
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia.
authors.forename: John
authors.initials: J
authors.lastname: Li
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia.
authors.forename: May May
authors.initials: MM
authors.lastname: Leong
authors.affiliation: Department of Pharmacology and Therapeutics, The University of Melbourne, Parkville, Victoria, 3010, Australia.
authors.forename: Alastair
authors.initials: A
authors.lastname: Stewart
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Rizzacasa
keywords: Sonogashira coupling; Wittig reaction; catalysis; eicosanoid; natural product; resolvin D2; total synthesis