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  • Title: A bio-inspired total synthesis of tetrahydrofuran lignans.
    Author: Albertson AK, Lumb JP.
    Journal: Angew Chem Int Ed Engl; 2015 Feb 09; 54(7):2204-8. PubMed ID: 25582827.
    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.
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