Example 1
1. Materials and Methods
Experimental
All buffers and reagents were obtained from Fisher Scientific or Sigma-Aldrich and used without further purification. Synthetic reactions were monitored by TLC using precoated silica gel plates (Silicycle 60F254, 0.25 mm thickness). Compounds were detected by ultraviolet light (λ=254 nm) followed by visualization with ammonium molybdate (10% w/v in 2M H2SO4), permanganate (1% w/v in water), or ninhydrin (1.5% w/v solution in butanol), with heating. Flash chromatography was performed using Silicyle silica gel (230-400 mesh). NMR spectra were obtained using a Varian Unity Inova 500 MHz spectrometer dissolving samples in the appropriate deuterated solvents (CDCl3, or CD3OD). Chemical shifts were reported in ppm downfield from tetramethylsilane. Low resolution ESI mass spectrometry was performed on an Advion Expression CMS Mass Spectrometer.
The compounds in the synthetic procedures of Example 1 are present as a mixture of enantiomers having the following stereochemical configurations: