Total Synthesis of (+)-Ribostamycin

Key words

(+)-ribostamycin - aminoglycosides - dearomative hydroamination - glycosylation - urazole

Significance

Sarlah, Liu, and co-workers developed a rapid route to access (+)-ribostamycin, an aminoglycoside (AG) featuring a central 1,3-diaminocyclohexanetriol moiety. AGs are a well-known class of carbohydrate-derived antibiotics, which suppress protein synthesis by binding to prokaryotic rRNA.

Comment

The key step in the construction of (+)-ribostamycin is an initial enantioselective dearomative hydroamination of benzene. Deprotection of urazole F initiates an intramolecular ­epoxide opening forming an urazole-bridged hetero­bicyclic system G. After two glycosylation ­reactions, the urazole is fragmented and a global reduction releases the natural product without the need for further purification.

Publication History

Article published online:
18 July 2022