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

18 May 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Photochemical rearrangement
Flow process
Chromene
Oxacycles
herbicide
Ring expansion

Supplementary materials

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Supporting information
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Supporting tables and schemes Experimental procedures Copies of NMR spectra
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