The radulanins are biologically active bibenzyl natural products featuring a synthetically challenging 2,5-dihydro-1-benzoxepine core. In contrast with previous reports exhibiting lengthy strategies, we demonstrate the shortest synthesis of radulanin A to date, featuring a largely unexplored photochemical ring expansion reaction of a 2,2-dimethylchromene precursor. This work was adapted to a continuous flow setup for larger scale preparation, in view of biological investigations into the herbicidal properties of this natural product.
An anion‐binding approach to the problem of preparing enantioenriched γ‐lactams from enolisable anhydrides and imines is reported. A simple bisurea catalyst promotes the cycloaddition between α‐aryl succinic anhydrides and either PMP‐ or benzhydryl‐protected aldimines to provide γ‐lactams with two contiguous stereocentres (one quaternary) with complete diastereocontrol and high to excellent enantioselectivity for the first time. A DFT study has provided insight into the catalyst mode of action and the origins of the observed stereocontrol.
A combination of experimental and computational techniques has shown that the mechanism of the base-catalysed Tamura cycloaddition is not a concerted Diels–Alder process.
The radulanins are biologically active bibenzyl natural products featuring a synthetically challenging 2,5-dihydro-1-benzoxepine core. In contrast with previous reports exhibiting lengthy strategies, we demonstrate the shortest synthesis of radulanin A to date, featuring a largely unexplored photochemical ring expansion reaction of a 2,2-dimethylchromene precursor. This work was adapted to a continuous flow setup for larger scale preparation, in view of biological investigations into the herbicidal properties of this natural product.
The radulanins are biologically active bibenzyl natural products featuring a synthetically challenging 2,5-dihydro-1-benzoxepine core. In contrast with previous reports exhibiting lengthy strategies, we demonstrate the shortest synthesis of radulanin A to date, featuring a largely unexplored photochemical ring expansion reaction of a 2,2-dimethylchromene precursor. This work was adapted to a continuous flow setup for larger scale preparation, in view of biological investigations into the herbicidal properties of this natural product.
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