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Synfacts 2022; 18(01): 0097
DOI: 10.1055/s-0041-1737162
Chemistry in Medicine and Biology

Hygromycin A Finds a New Purpose

Contributor(s):
Dirk Trauner
,
Anna C. Impastato
Chida N, Ohtuska M, Nakazawa K, Ogawa S. * Keio University, Yokohama, Japan
Total Synthesis of Antibiotic Hygromycin A.

J. Org. Chem. 1991;
56: 2976-2983
DOI: 10.1021/jo00009a009.
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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.


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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.


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Publication History

Article published online:
17 December 2021

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