Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2012.10.059

Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

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

19 Scopus citations

Abstract

The total synthesis of Resolvin D1, a potent endogenous anti-inflammatory lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C7, C8 and C17 were obtained via a chiral pool strategy from 2-deoxy-d-ribose. Wittig reactions followed by a modified Pd⁰/Cu ^I Sonogashira coupling and Zn(Cu/Ag) cis-reduction completed the total synthesis of Resolvin D1.

Original language	English (US)
Pages (from-to)	6990-6994
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2012.10.059
State	Published - Dec 19 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.10.059

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title = "Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator",

abstract = "The total synthesis of Resolvin D1, a potent endogenous anti-inflammatory lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C7, C8 and C17 were obtained via a chiral pool strategy from 2-deoxy-d-ribose. Wittig reactions followed by a modified Pd0/Cu I Sonogashira coupling and Zn(Cu/Ag) cis-reduction completed the total synthesis of Resolvin D1.",

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T1 - Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator

AU - Rodriguez, Ana R.

AU - Spur, Bernd W.

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N2 - The total synthesis of Resolvin D1, a potent endogenous anti-inflammatory lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C7, C8 and C17 were obtained via a chiral pool strategy from 2-deoxy-d-ribose. Wittig reactions followed by a modified Pd0/Cu I Sonogashira coupling and Zn(Cu/Ag) cis-reduction completed the total synthesis of Resolvin D1.

AB - The total synthesis of Resolvin D1, a potent endogenous anti-inflammatory lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C7, C8 and C17 were obtained via a chiral pool strategy from 2-deoxy-d-ribose. Wittig reactions followed by a modified Pd0/Cu I Sonogashira coupling and Zn(Cu/Ag) cis-reduction completed the total synthesis of Resolvin D1.

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UR - https://www.scopus.com/pages/publications/84869232273#tab=citedBy

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DO - 10.1016/j.tetlet.2012.10.059

M3 - Article

AN - SCOPUS:84869232273

SN - 0040-4039

VL - 53

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EP - 6994

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator

Abstract

All Science Journal Classification (ASJC) codes

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