First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2011.11.003

First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

Ana R. Rodriguez, Bernd W. Spur

Cell Biology

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

37 Scopus citations

Abstract

The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd⁰/Cu^I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.

Original language	English (US)
Pages (from-to)	86-89
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.003
State	Published - Jan 4 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.11.003

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abstract = "The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.",

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AU - Spur, Bernd W.

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N2 - The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.

AB - The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.

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First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

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