Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2022

Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-03781949 , version 1 (20-09-2022)

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Bruce Lockett-Walters, Simon Thuillier, Emmanuel Baudouin, Bastien Nay. Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow. Organic Letters, 2022, 24 (22), pp.4029 - 4033. ⟨10.1021/acs.orglett.2c01462⟩. ⟨hal-03781949⟩
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