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Enantioselective Synthesis, Stereochemical Correction, and Biological Investigation of the Rodgersinine Family of 1,4-Benzodioxane Neolignans

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journal contribution
posted on 20.02.2015, 00:00 by Lisa I. Pilkington, Jessica Wagoner, Stephen J. Polyak, David Barker
The enantioselective synthesis and chiroptic analysis of all members of the rodgersinine family of 1,4-benzodioxane neolignans has been achieved. ECD spectra and optical rotation analysis determined that the previously published stereochemistry of trans-rodgersinines A and B was incorrect. The cis-rodgersinines A and B did not follow the model ECD study commonly used to assign the absolute stereochemistry of 1,4-benzodioxane natural products. This finding has implications on the absolute stereochemistry of other natural products of this type. Additionally, the rodgersinines were found to have anti-HCV activities.