Organic Chemistry

A concise total synthesis of phytotoxic radulanin A facilitated by the photochemical ring expansion of a 2,2-dimethylchromene in flow

Authors

Abstract

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.

Content

Thumbnail image of radA ChemRXiv.pdf

Supplementary material

Thumbnail image of RadA ESI.pdf
Supporting information
Supporting tables and schemes Experimental procedures Copies of NMR spectra