Issue 8, 2019

Stereocontrolled synthesis of resolvin D1

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Dec 2018
Accepted
29 Jan 2019
First published
30 Jan 2019

Org. Biomol. Chem., 2019,17, 2212-2222

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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