(18R)- and (18S)-resolvins E3 were synthesized via the Pd-catalyzed addition of AcOH to the syn and anti isomers of vinyl epoxy alcohols.

Two trans-enynyl alcohol intermediates corresponding to the C1–C8 and C13–C22 parts of resolvin D6 (RvD6) were prepared through the Hudrlik–Peterson reaction of the TMS-substituted trans-epoxy alcohols with TMS-acetylide and subsequent TMS-desilylation. These intermediates were coupled with a 1,4-dihalo-2-butyne derivative under copper catalysis, and the resulting acetylene was reduced with Zn(Cu/Ag) to afford the TBS ether of RvD6 methyl ester. Desilylation with TBAF yielded the γ-lactone of RvD6, which was hydrolyzed to RvD6. The total yield of RvD6 was 1.9% in 19 steps from (3-trimethylsilyl)propargyl alcohol. The TBS ether of RvE2 methyl ester was also synthesized.

No abstract

-Derivatization of secondary alcohols (R 1 R 2 CHOH) to benzoates has frequently employed to determine enantiomer ratios using HPLC with chiral stationary phase (CSP). However, a small difference in substituents (R 1 , R 2 ) often results in insufficient separation. To find an alternative derivatization that detects such a small difference, picolinates (2-pyridyl-CO 2 CHR 1 R 2 ) possessing Me/Et, Me/vinyl, Me/acetylenic, Et/n-Pr, and n-Pr/allyl substituents were prepared and separation efficiency was compared with that of benzoates (PhCO 2 CHR 1 R 2 ).Eight commercially available CSPs containing carbamates or benzoates of cellulose and amylose were examined to find that retention factors (k' 1 and k' 2 ) and resolution (R s ) of picolinates were greater than those of the corresponding benzoates and that good to excellent R s values (≥1.25) were recorded over a wide range of CSPs.