title: Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor.
abstract: Streptolydigin is a highly potent, broad-spectrum antibiotic produced by Streptomyces lydicus, which inhibits bacterial RNA polymerase. We describe the first synthesis of streptolydigin, which was assembled in a highly convergent and fully stereocontrolled fashion with a longest linear sequence of 24 steps starting from commercially available precursors. The assembly process entailed preparation of fully elaborated streptolic and ydiginic subunits of the natural product, followed by a highly efficient union in a three-step one-pot procedure, which included Dieckmann cyclization with a concomitant imide opening, Horner-Wadsworth-Emmons olefination, and desilylation.
authors.affiliation: University of Chicago, Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Sergey V
authors.initials: SV
authors.lastname: Pronin
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Kozmin
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors*; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000617:Aminoglycosides; C100307:streptolydigin; D012321:DNA-Directed RNA Polymerases