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An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by 1H NMR Spectroscopy
Si-Yuan Shao1, Ya-Nan Yang1, Zi-Ming Feng1
1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.
Abstract:
An efficient 1H NMR spectroscopic approach for determining the relative configurations of lignans with a 7,9':7',9-diepoxy moiety has been established. Using the chemical shift differences of H2-9 and H2-9' (ΔδH-9 and ΔδH-9'), the configurations of 8-H and 8-OH furofuran lignans can be rapidly and conveniently determined. The rule is applicable for data acquired in DMSO- d6, methanol- d4, or CDCl3. Notably, the rule should be applied carefully when the C-2 or C-6 substituent of the aromatic rings may alter the dominant conformers of the furofuran moiety.
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