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Synfacts 2022; 18(01): 0085
DOI: 10.1055/s-0041-1737169
Chemistry in Medicine and Biology

The Next Generation Lincosamide: Iboxamycin

Contributor(s):
Dirk Trauner
,
Klaus-Peter Ruehmann
Polikanov YS, *, Myers AG. * et al. University of Illinois at Chicago and Harvard University, Cambridge, USA
A Synthetic Antibiotic Class Overcoming Bacterial Multidrug Resistance.

Nature 2021;
599: 507-512
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Mitcheltree MJ, Stevenson JW, Pisipati A, Myers AG. * Harvard University, Cambridge, USA
A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics.

J. Am. Chem. Soc. 2021;
143: 6829-6835
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Key words

antibiotics - Sharpless epoxidation - pseudoephenamine auxiliary - ring-closing metathesis - Wacker oxidation

Significance

The lincosamides are a class of antibiotics that acts by inhibition of the bacterial ribosome. 50 years after the semisynthetic derivative clindamycin was approved by the FDA, Myers and co-workers published their component-based total synthetic platform, which resulted in a new, highly potent lincosamide analogue: iboxamycin. It acts in Gram-positive, Gram-negative, and resistant strains.


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Comment

The lincosamine northern half was accessed from an epoxy aldehyde and a nitro compound A. The diastereoselective Henry reaction between both building blocks was followed by an epoxide opening that established a cyclic nitronate. Hydroxyproline analogues of the southern half were accessed using the Myers’ pseudoephanamine auxiliary.


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Publication History

Article published online:
17 December 2021

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