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

33 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

Access to Document

10.1016/j.tetlet.2012.05.143

Cite this

@article{d913d369f78d480d9900bd63989ce76c,

title = "Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1",

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.",

author = "Rodriguez, {Ana R.} and Spur, {Bernd W.}",

year = "2012",

month = aug,

day = "8",

doi = "10.1016/j.tetlet.2012.05.143",

language = "English (US)",

volume = "53",

pages = "4169--4172",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "32",

}

TY - JOUR

T1 - Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

AU - Rodriguez, Ana R.

AU - Spur, Bernd W.

PY - 2012/8/8

Y1 - 2012/8/8

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.

UR - http://www.scopus.com/inward/record.url?scp=84863618373&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84863618373&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.05.143

DO - 10.1016/j.tetlet.2012.05.143

M3 - Article

AN - SCOPUS:84863618373

SN - 0040-4039

VL - 53

SP - 4169

EP - 4172

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this