Ungarean CN,
Galer P,
Zhang Y,
Lee KS,
Ngai JM,
Lee S,
Liu P,
*,
Sarlah D.
*
University of Pittsburgh and University of Illinois, Urbana, USA
Synthesis of (+)-Ribostamycin by Catalytic, Enantioselective Hydroamination of Benzene.
Nat. Synth. 2022;
DOI:
10.1038/s44160-022-00080-x
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.
