Stereocontrolled synthesis of resolvin D1

Org Biomol Chem. 2019 Feb 20;17(8):2212-2222. doi: 10.1039/c8ob03128b.

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.

Publication types

  • Research Support, Non-U.S. Gov't