Total synthesis of the anti-inflammatory lipid mediator Resolvin E2

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2012.01.136

Total synthesis of the anti-inflammatory lipid mediator Resolvin E2

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

The total synthesis of Resolvin E2, an endogenous lipid mediator of the resolution of inflammation derived from eicosapentaenoic acid, has been achieved. The chiral hydroxy-groups at C5 and C18 were generated in a simple, efficient, and environmentally friendly manner via an asymmetric Noyori transfer hydrogenation in water using sodium formate as a reducing agent. Pd ⁰/Cu ^I Sonogashira couplings of the three key fragments and Zn(Cu/Ag) reduction completed the synthesis of Resolvin E2.

Original language	English (US)
Pages (from-to)	1912-1915
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2012.01.136
State	Published - Apr 11 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.01.136

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abstract = "The total synthesis of Resolvin E2, an endogenous lipid mediator of the resolution of inflammation derived from eicosapentaenoic acid, has been achieved. The chiral hydroxy-groups at C5 and C18 were generated in a simple, efficient, and environmentally friendly manner via an asymmetric Noyori transfer hydrogenation in water using sodium formate as a reducing agent. Pd 0/Cu I Sonogashira couplings of the three key fragments and Zn(Cu/Ag) reduction completed the synthesis of Resolvin E2.",

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AB - The total synthesis of Resolvin E2, an endogenous lipid mediator of the resolution of inflammation derived from eicosapentaenoic acid, has been achieved. The chiral hydroxy-groups at C5 and C18 were generated in a simple, efficient, and environmentally friendly manner via an asymmetric Noyori transfer hydrogenation in water using sodium formate as a reducing agent. Pd 0/Cu I Sonogashira couplings of the three key fragments and Zn(Cu/Ag) reduction completed the synthesis of Resolvin E2.

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M3 - Article

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EP - 1915

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Total synthesis of the anti-inflammatory lipid mediator Resolvin E2

Abstract

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