Sulfamate-tethered aza-Wacker approach towards analogs of Bactobolin A

Here, we describe an approach towards analogs of the potent antibiotic Bactobolin A. Sulfamate-tethered aza -Wacker cyclization reactions furnish key synthons, which we envision can be elaborated into analogs of Bactobolin A. Docking studies show that the C4 epimer of Bactobolin A and the C4/C6 diastereomer interact with different residues of the 23S rRNA (bacterial ribosome 50S subunit) than the natural product, suggesting that these molecules could be valuable tool compounds for fundamental studies of the bacterial translational machinery.