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A Bio‐Inspired Total Synthesis of Tetrahydrofuran Lignans
Author(s) -
Albertson Anna K. F.,
Lumb JeanPhilip
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408641
Subject(s) - lignan , pinoresinol , total synthesis , oxidative coupling of methane , chemistry , biomimetic synthesis , ferulic acid , phenols , tetrahydrofuran , stereochemistry , propenyl , enantioselective synthesis , combinatorial chemistry , organic chemistry , biochemistry , methane , solvent , catalysis
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.