First total synthesis of pro-resolving and tissue-regenerative Maresin sulfido-conjugates

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2015.04.131

First total synthesis of pro-resolving and tissue-regenerative Maresin sulfido-conjugates

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

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

18 Scopus citations

Abstract

The first stereospecific total synthesis of the pro-resolving and tissue-regenerative Maresin sulfido-conjugates: 13R,14S-MCTR1, 13R,14S-MCTR2 and 13R,14S-MCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 13S,14S-epoxy-Maresin methyl ester was synthesized using a chiral pool strategy starting from 2-deoxy-d-ribose. Wittig reactions, selective epoxide formation and epoxide opening with glutathione, l-cysteinylglycine and l-cysteine methyl ester hydrochloride respectively, were the key steps in the synthesis.

Original language	English (US)
Pages (from-to)	3936-3940
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2015.04.131
State	Published - May 30 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "First total synthesis of pro-resolving and tissue-regenerative Maresin sulfido-conjugates",

abstract = "The first stereospecific total synthesis of the pro-resolving and tissue-regenerative Maresin sulfido-conjugates: 13R,14S-MCTR1, 13R,14S-MCTR2 and 13R,14S-MCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 13S,14S-epoxy-Maresin methyl ester was synthesized using a chiral pool strategy starting from 2-deoxy-d-ribose. Wittig reactions, selective epoxide formation and epoxide opening with glutathione, l-cysteinylglycine and l-cysteine methyl ester hydrochloride respectively, were the key steps in the synthesis.",

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AU - Rodriguez, Ana R.

AU - Spur, Bernd W.

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N2 - The first stereospecific total synthesis of the pro-resolving and tissue-regenerative Maresin sulfido-conjugates: 13R,14S-MCTR1, 13R,14S-MCTR2 and 13R,14S-MCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 13S,14S-epoxy-Maresin methyl ester was synthesized using a chiral pool strategy starting from 2-deoxy-d-ribose. Wittig reactions, selective epoxide formation and epoxide opening with glutathione, l-cysteinylglycine and l-cysteine methyl ester hydrochloride respectively, were the key steps in the synthesis.

AB - The first stereospecific total synthesis of the pro-resolving and tissue-regenerative Maresin sulfido-conjugates: 13R,14S-MCTR1, 13R,14S-MCTR2 and 13R,14S-MCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 13S,14S-epoxy-Maresin methyl ester was synthesized using a chiral pool strategy starting from 2-deoxy-d-ribose. Wittig reactions, selective epoxide formation and epoxide opening with glutathione, l-cysteinylglycine and l-cysteine methyl ester hydrochloride respectively, were the key steps in the synthesis.

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DO - 10.1016/j.tetlet.2015.04.131

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

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First total synthesis of pro-resolving and tissue-regenerative Maresin sulfido-conjugates

Abstract

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