Triphenylphosine

The following reagents were obtained from Sigma Co. (St. Louis, MO, USA): catechin, kaempferol, isorhamnetin, naringenin, quercetin, butylated hydroxytoluene (BHT), Folin–Ciocalteu’s phenol reagent, copper sulfate, ethylenediaminetetraacetic acid (EDTA), β-glucuronidase type H-2 (containing sulfatase from Helix pomatia), glutathione reductase (type III), nicotinamide adenine dinucleotide phosphate (NADP), sodium 1-octanesulfonate monohydrate, reduced glutathione, oxidized glutathione, sodium azide, sodium chloride, sodium phosphate monobasic, sodium phosphate dibasic, 1,1,3,3-tetraethoxypropane, 2’,3’,4’-trihydroxyacetophenone, Tris buffer, magnesium chloride, triphenylphosine, and α-tocopherol. Diisopropylethylamine (DIPEA), O-bis (trimethylsilyl) trifluoroacetamide (BSTFA), and pentafluorobenzyl bromide (PFBBr) were purchased from Thermo (Boston, MA, USA). Deuterated prostaglandin (PG) F_2α (internal standard), PGF_2β, and 8-iso-PGF_2α were purchased from Cayman (Ann Arbor, MI, USA). All organic solvents, glacial acetic acid, and potassium bromide were purchased from Fisher Co. (Fair Lawn, NJ, USA).

Anhydrous magnesium sulfate (MgSO₄, 99.5%), pyrene (Py), benzophenone (99%), PdCl₂(PPh₃)₂, bromine solution (Br₂), copper(I) iodide (CuI, 99%), dichloromethane (DCM), glacial acetic acid (AcOH), hydrogen peroxide (H₂O₂), potassium carbonate (K₂CO₃, 99.9%), Pd(PPh₃)₄, thianthrene (THT, 99%), titanium tetrachloride (TiCl₄, 99.9%), trimethylsilylacetylene (TMSA, 98%), triphenylphosine (PPh₃, 99%), zinc powder (Zn, 98%) were purchased from Sigma-Aldrich (Gillingham, UK) and Acros Organics (Geel, Belgium).