Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2012.05.143

Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

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

36 Scopus citations

Abstract

The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd ⁰/Cu ^I Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.

Original language	English (US)
Pages (from-to)	4169-4172
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2012.05.143
State	Published - Aug 8 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.05.143

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abstract = "The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd 0/Cu I Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.",

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AU - Spur, Bernd W.

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N2 - The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd 0/Cu I Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.

AB - The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd 0/Cu I Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.

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UR - https://www.scopus.com/pages/publications/84863618373#tab=citedBy

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M3 - Article

AN - SCOPUS:84863618373

SN - 0040-4039

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EP - 4172

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

Abstract

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