Total synthesis of decarboxyaltenusin

Beilstein J Org Chem. 2021 Jan 22:17:224-228. doi: 10.3762/bjoc.17.22. eCollection 2021.

Abstract

The total synthesis of decarboxyaltenusin (5'-methoxy-6-methyl-[1,1'-biphenyl]-3,3',4-triol), a toxin produced by various mold fungi, has been achieved in seven steps in a yield of 31% starting from 4-methylcatechol and 1-bromo-3,5-dimethoxybenzene, where the longest linear sequence consists of five steps. The key reaction was a palladium-catalyzed Suzuki coupling of an aromatic boronate with a brominated resorcin derivative.

Keywords: Suzuki coupling; biaryls; boronates; mycotoxins; polyketides.

Grants and funding

The work was supported by the Helmholtz Program Biointerfaces in Technology and Medicine (BIFTM).