Streptothricin F is a member of the streptothricin natural products class and is highly active against Gram-positive and Gram-negative pathogens of resistance-concern and many members of the so-called ESKAPE pathogens. Through cryo-EM characterization, we have identified a novel binding site of streptothricin F within the ribosome of Gram-negative <i>Acinetobacter baumannii</i>. Despite potent activity, the streptothricins have not been systematically pursued in drug discovery efforts due to toxicity and resistance concerns. We have completed a convergent, diversity-enabling total synthesis of streptothricin F consisting of 35 total steps and an overall yield of 0.40%. Using this fully developed streptothricin F synthesis, we are pursuing the synthesis of both previously reported and novel analogs of the streptothricin class.

Convergent total synthesis of streptothricin analogs

ACS Spring 2022

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