Pump module c 605

IR spectra were measured using an FT/IR-4100 spectrometer (JASCO, Tokyo, Japan). Ultraviolet (UV) spectra were obtained using a V-530 spectrometer (JASCO). CD spectrum was taken on a J-720WN spectrometer (JASCO). Specific rotations were recorded on a DIP-370 spectrometer (JASCO). High-resolution mass spectra (HRMS) were acquired on a Mariner Biospectrometry Workstation (Thermo Fisher Scientific (former Applied Biosystems), Waltham, MA, USA) in the positive electrospray ionization (ESI) mode using 80% MeOH-0.1% HCOOH and 80% MeOH-1 mM HCOONa for enhygromic (1) acid and deoxyenhygrolides (2 and 3), respectively, as the infusion solvent. NMR spectra were obtained on an Avance 400 (400 MHz) or Avance III HD 600 Cryo-Probe (600 MHz) spectrometer (Bruker BioSpin, Yokohama, Japan). The chemical shifts (ppm) were referenced to the solvent (DMSO-d₆ or C₆D₆) peaks. Flash column chromatography was carried out with a medium-pressure gradient system equipped with a Pump Module C-605 and a Pump Manager C-615 (BÜCHI, Flawil, Switzerland). Preparative high-performance liquid chromatography (HPLC) was performed on a high-pressure gradient system composed of a PU-2087 pump, a DG-2080-53 degasser, an MX-2080-32 mixer, and a UV-2075 detector (JASCO). Melting point was measured on a micro melting point apparatus MP-J3 (Yanaco, Kyoto, Japan).

Thin layer chromatography (TLC) was conducted by using precoated silica gel 600 F254 plates (Art. 5715, Merck, Darmstadt, Germany) or reverse phase C18 F254 plates (Art. 15389, Merck, Darmstadt, Germany). Flash column chromatography was carried out on silica gel by a medium-pressure gradient system equipped with a Pump Module C-605 and a Pump Manager C-615 (BÜCHI, Flawil, Switzerland). High resolution ESIMS were recorded on a Mariner Biospectrometry Workstation (Applied Biosystems of Thermo Fisher Scientific, Waltham, MA, USA) equipped with an electrospray ion source in the positive mode. High performance liquid chromatography (HPLC) was performed on a high pressure gradient system that is composed of pumps PU-2087, a degasser DG-2080-53, a mixer MX-2080-32, and a detector UV-2075 (JASCO, Tokyo, Japan). FT-IR spectra were recorded on an FT/IR-400 spectrometer instrument (JASCO). Specific rotations were observed on a DIP-370 polarimeter (JASCO). NMR spectra were investigated on an Avance ARX400 (400 MHz for ¹H) or Avance III HD 600 MHz Cryo-probe spectrometer (600 MHz for ¹H) (Bruker Bio Spin, Yokohama, Japan). The chemical shifts (ppm) were referenced to the solvent residual peak at δ_H 7.26 ppm (CDCl₃), δ_H 3.30/δ_C 49.0 ppm (CD₃OD), or δ_H 2.06/δ_C 29.9 ppm (acetone-d₆).

Flash chromatography was carried out with a medium-pressure gradient system equipped with a Pump Module C-605 and a Pump Manager C-615 (BÜCHI, Flawil, Switzerland). Preparative HPLC was performed on a high-pressure gradient system equipped with PU-2087 plus pumps and a UV-2075 plus detector (Jasco, Tokyo, Japan). Specific rotation was measured by using a DIP-370 digital polarimeter (Jasco). FT-IR and UV spectra were recorded on FT/IR-4100 and V-530 spectrometers (Jasco), respectively. Mass spectra (MS) were recorded on a Mariner Biospectrometry Workstation (Applied Biosystems of Thermo Fisher Scientific, Waltham, MA, USA) in the positive-ESI mode. ¹H- and ¹³C-NMR spectra were recorded at 27 °C on an Avance 400 (400 MHz for ¹H) or Avance III HD 600 Cryo-Probe (600 MHz for ¹H) spectrometer (Bruker, Rheinstetten, Germany). Chemical shifts (ppm) were referenced to the solvent (CDCl₃) peaks at δ_H 7.26 ppm (residual CHCl₃) and δ_C 77.0 ppm.