Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates

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Abstract

The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs<inf>2</inf>CO<inf>3</inf> promoted coupling provided the skipped diyne intermediate. Wittig reactions 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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Rodriguez, A. R., & Spur, B. W. (2015). Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates. Tetrahedron Letters, 56(42), 5811–5815. https://doi.org/10.1016/j.tetlet.2015.09.020

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