Kiselgel 60

All other reagents used in this work were purchased from (Sigma-Aldrich Saint Louis, Missouri, USA). ¹H NMR and ¹³C NMR spectra were recorded in solutions (CDCl₃ with c.a. 1% TMS) on Bruker Avance DRX 600 spectrometer. IR spectra were recorded on a PerkinElmer Spectrum 400. HR-ESI-MS spectra were recorded on Bruker micrOTOF-Q II with ionization ESI. Analytical gas chromatography (GC) was performed on a Thermo Scientific-Trace 1310 apparatus using TG-5HT (30 m × 0.25 mm) capillary column. Analytical thin layer chromatography (TLC) was carried out on silica gel G (Merck), and various developing systems were applied. Compounds detected by I₂ in the iodide chamber. Column chromatography was performed on silica gel (Kiselgel 60, 230–400 mesh, Merck) with hexane-ethyl acetate and hexane-acetone. Chemical shifts are expressed in parts per million using TMS as an internal standard.

Column chromatography was performed using Kiselgel 60 (Merck, Art. 7734, Art. 9385, NJ, USA) and RP-18 (YMC, Art. 14878, Japan). All purifications were monitored using thin-layer chromatography (TLC) precoated with Kiselgel 60 F₂₅₄ (Merck, Art. 5715). Compound purifications were performed using a high-performance liquid chromatography (HPLC) core system (Thermo Scientific, Germering, Germany; Dionex Ultimate 3000 Diode Array with ELSD at 254, 280, and 365 nm; and a Dionex Ultimate 3000 pump). A Kinetex 5 μm C18 100 Å (250 × 4.6 mm, Phenomenex, CA, USA) column was used for isolation. The mobile phase consisted of solvent A (water with 0.1% acetic acid) and solvent B (MeOH with 0.1% acetic acid) at a flow rate of 1.0 mL/min. The injection volume was 10 μL, and the column temperature was 35 °C. The ¹H-NMR spectrum was recorded using a Bruker Avance Digital 500 spectrometer (Karlsruhe, Germany) at 500 MHz. Chemical shifts were provided as δ (ppm) from tetramethylsilane (TMS). All of the reagents were purchased from Sigma-Aldrich (St. Louis, MO, USA).