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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).

SUBMITTER: Li J

PROVIDER: S-EPMC3869264 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Li John J Leong May May MM Stewart Alastair A Rizzacasa Mark A MA

Beilstein journal of organic chemistry 20131203

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 reduct ...[more]

PMID: 24367439

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