Wakogel c 300e

1 H NMR spectra were recorded using a JEOL AL-400 or a JEOL ECA-500 spectrometer. Chemical shifts are reported in δ (ppm) relative to Me4Si as an internal standard. 13 C NMR spectra were referenced to the residual solvent signal. Exact mass (HRMS) spectra were recorded on a JMS-HX/HX 110A mass spectrometer or Shimadzu LC-ESI-IT-TOF-MS equipment. For flash chromatography, Wakogel C-300E (Wako) was employed. For analytical HPLC, a Cosmosil 5C18-ARII column (4.6  250 mm, Nacalai Tesque, Inc.) was employed with a linear gradient of CH3CN containing 0.1% (v/v) TFA aq. at a flow rate of 1 mL/min, and eluting products were detected by UV at 254 nm.
Preparative HPLC was performed using a Cosmosil 5C18-ARII preparative column (20  250 mm, Nacalai Tesque, Inc.) with a linear gradient of CH3CN containing 0.1% (v/v) TFA aq. at a flow rate of 8 mL/min. The purity of the compounds was determined as no less than 95% by combustion analysis or HPLC analysis.

General Methods 1 H-NMR spectra were recorded using a JEOL ECA-500 spectrometer at 500 MHz frequency. Chemical shifts are reported in δ (ppm) relative to Me 4 Si (in CDCl 3 ) as internal standard. 13 (link) C-NMR spectra were recorded using a JEOL ECA-500 and referenced to the residual CHCl 3 signal. Exact mass (HR-MS) spectra were recorded on a Shimadzu LC-ESI-IT-TOF-MS equipment (electrospray ionization (ESI)). Optical rotations were measured with a JASCO P-1020 polarimeter. For column chromatography, Wakogel C-300E (Wako, Osaka, Japan) or Chromatorex NH-DM1020 (Fuji Silysia, Japan) was employed.

1 H NMR spectra were recorded using a JEOL AL-400 or a JEOL ECA-500 spectrometer. Chemical shifts are reported in δ (ppm) relative to Me4Si as an internal standard. 13 C NMR spectra were recorded using a JEOL AL-400 or a JEOL ECA-500 and referenced to the residual solvent signal. Exact mass (HRMS) spectra were recorded on Shimadzu LC-ESI-IT-TOF-MS equipment. IR spectra were obtained on a JASCO FT/IR-4100 spectrometer. Melting points were measured by a hot stage melting points apparatus (uncorrected). Optical rotations were measured with a JASCO P-1020 polarimeter.
For chromatography, Wakogel C-300E (Wako) was employed. (158 mg, 1.00 mmol) in EtOH (2.00 mL) was added quinoline-2-carbohydrazide [28] (187 mg, 1.00 mmol). After being stirred for 17 h at 70 °C, the reaction mixture was concentrated. The residue was dissolved with EtOAc, and the whole was washed with 1 M NaOH and brine, and dried over Na2SO4.
After the filtrate was concentrated, the residue was purified by column chromatography on silica gel (n-hexane/EtOAc = 1/3) to give the title compound 6 (107 mg, 26%): pale yellow amorphous solid;
[α] 24