The Convergent Total Synthesis and Antibacterial Profile of the Natural Product Streptothricin F

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Apr 18

PMID 35432870

Authors

Matthew G Dowgiallo

Brandon C Miller

Mintesinot Kassu

Kenneth P Smith

Andrew D Fetigan

Jason J Guo

James E Kirby

Roman Manetsch

Affiliations

Soon will be listed here.

Abstract

A convergent, diversity-enabling total synthesis of the natural product streptothricin F has been achieved. Herein, we describe the potent antimicrobial activity of streptothricin F and highlight the importance of a total synthesis that allows for the installation of practical divergent steps for medicinal chemistry exploits. Key features of our synthesis include a Burgess reagent-mediated 1,2--diamine installation, diastereoselective azidation of a lactam enolate, and a mercury(ii) chloride-mediated desulfurization-guanidination. The development of this chemistry enables the synthesis and structure-activity studies of streptothricin F analogs.

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