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Issue 8, 2019
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Stereocontrolled synthesis of resolvin D1

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Abstract

We studied the synthesis of RvD1, a pro-resolving mediator. The intermediate containing vic-diol and enal functional groups was prepared via the oxidation of the γ,δ-epoxy alcohol followed by the epoxide ring opening in one pot. The C11-aldehyde in the resulting enal was converted to the trans iodo-olefin by reaction with TMSC(N2)Li and subsequent hydrozirconation using in situ generated Cp2Zr(H)Cl followed by iodination. The trans enynyl alcohol was synthesized by the reaction of the TMS-containing epoxy alcohol with lithium TMS-acetylide. Finally, two fragments were joined by the Sonogashira coupling, and the triple bond was reduced to afford RvD1 stereoselectively.

Graphical abstract: Stereocontrolled synthesis of resolvin D1

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Publication details

The article was received on 17 Dec 2018, accepted on 29 Jan 2019 and first published on 30 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03128B
Org. Biomol. Chem., 2019,17, 2212-2222

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    Stereocontrolled synthesis of resolvin D1

    M. Morita, S. Wu and Y. Kobayashi, Org. Biomol. Chem., 2019, 17, 2212
    DOI: 10.1039/C8OB03128B

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