Hygromycin A Finds a New Purpose

Key words

Ferrier carbocyclization - Wittig reaction - Sharpless dihydroxylation - drug repurposing

Significance

Hygromycin A is a broad-spectrum antibiotic produced by Streptomyces. It was recently rediscovered as a potential therapy for the treatment of Lyme Disease (Cell 2021, 184, 5405). In mouse models, Hygromycin A was active against B. burgdorferi without disturbing the microbiome.

Comment

The first total synthesis of Hygromycin A was reported by Ogawa and co-workers in 1991. Key transformations included a Ferrier carbocyclization and a Sharpless dihydroxylation to form building block A. The furanose and aminocyclitol fragments were pieced together using a Wittig reaction followed by a Yamada peptide coupling.

Publikationsverlauf

Artikel online veröffentlicht:
17. Dezember 2021