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Updated: Jun 29, 2026

Synthesis of Masarimycin, a Small Molecule Inhibitor of Gram-Positive Bacterial Growth
Published on: January 7, 2022
Stereochemical assignment and first synthesis of the core of miharamycin antibiotics
Filipa Marcelo1, Jesús Jiménez-Barbero, Jérôme Marrot
1UMR 7611, Equipe Glycochimie, UPMC-Paris 6, 4 place Jussieu, Paris, France.
Abstract:
The relative configuration at C-6' of nucleoside antibiotic miharamycin A has been elucidated by NMR spectroscopy and proved to be S. The total synthesis of miharamycin B has also been investigated, which has led to the unprecedented construction of its core. The bicyclic sugar moiety has been elaborated by means of a SmI(2)-based keto-alkyne coupling. Elongation of its C-6 position towards a bicyclic sugar amino acid and conversion into a suitable glycosyl donor enabled efficient N-glycosylation with 2-aminopurine to take place to afford the nucleosidic part of miharamycin B. Final peptide coupling with arginine afforded the skeleton of miharamycin B. Unfortunately, attempts to deprotect this scaffold failed to afford the complex nucleoside antibiotic.
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