title: Enantioselective synthesis, stereochemical correction, and biological investigation of the rodgersinine family of 1,4-benzodioxane neolignans.
abstract: 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.
authors: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors: Lisa I
authors: LI
authors: Pilkington
authors: Jessica
authors: J
authors: Wagoner
authors: Stephen J
authors: SJ
authors: Polyak
authors: David
authors: D
authors: Barker
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016174:Hepacivirus / Q000187:drug effects; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000998:Antiviral Agents; D001688:Biological Products; D004146:Dioxanes; D017705:Lignans; C000600193:rodgersinine A; C000600194:rodgersinine B