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Article Abstract
A modular approach to the potent, broad-spectrum antibiotic amycolamicin and seven diastereomeric analogues is described. The synthesis features bioinspired construction of the high-carbon amycolose segment, gold(I)-catalyzed high-yielding -glycosylation of the -decalin scaffold, -glycosylation of the bromoacetylated l-valine derivative, and condition-tuned late-stage -acylation of the tetramic acid motif. An assessment of the antibacterial properties of these synthetic molecules indicated that the correct stereochemistry is essential for the potent bioactivity of amycolamicin.
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