Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2014.09.007

Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

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

16 Scopus citations

Abstract

The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd⁰/Cu^ISonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1.

Original language	English (US)
Pages (from-to)	6011-6015
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2014.09.007
State	Published - Oct 22 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.09.007

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abstract = "The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd0/CuISonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1.",

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AU - Rodriguez, Ana R.

AU - Spur, Bernd W.

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N2 - The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd0/CuISonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1.

AB - The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd0/CuISonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1.

UR - https://www.scopus.com/pages/publications/84907572510

UR - https://www.scopus.com/pages/publications/84907572510#tab=citedBy

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DO - 10.1016/j.tetlet.2014.09.007

M3 - Article

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SN - 0040-4039

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SP - 6011

EP - 6015

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1

Abstract

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