First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

Ana R. Rodríguez; Bernd W. Spur

doi:10.1016/j.tetlet.2005.03.175

First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

Ana R. Rodríguez, Bernd W. Spur

Cell Biology

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44 Scopus citations

Abstract

The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd⁰/Cu ^I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.

Original language	English (US)
Pages (from-to)	3623-3627
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.175
State	Published - May 23 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.03.175

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abstract = "The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd0/Cu I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.",

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AU - Spur, Bernd W.

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AB - The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd0/Cu I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.

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First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

Abstract

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