title: A bio-inspired total synthesis of tetrahydrofuran lignans.
abstract: Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regio- and chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8 (Canada).
authors.forename: Anna K F
authors.initials: AK
authors.lastname: Albertson
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
mesh_terms: D032701:Biomimetics; D003373:Coumaric Acids / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D017705:Lignans / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry
chemical_list: D003373:Coumaric Acids; D005663:Furans; D017705:Lignans; D010636:Phenols; C493882:tanegool; C018674:tetrahydrofuran; C004999:ferulic acid; C103298:pinoresinol
keywords: biomimetic synthesis; cascade reactions; lignans; natural products; phenolic oxidation