The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach (original) (raw)
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1964
The history of the chemotherapy of tuberculosis is reviewed, with emphasis on the newer experimental drugs such as ethambutol, kanamycin and 4,4'-di-isoamyl oxythiocarbanilide. The recognised regimens in tuberculo-therapy are discussed briefly in order that the current status of streptomycin may be appreciated. The chemistry of the aminoglycoside antibiotics is reviewed in detail, evidence of the recently assigned structures of the neomycin-paromomycin group and the kanamycins being cited as well as the more classical degradation and structural determination of streptomycin. Suggested biogenetic pathways and recent mode of action studies are noted, the introduction being completed by an inventory of synthetic derivatives of this group of antibiotics. The remaining points of the chemistry of dihydrostreptomycin to be elucidated are discussed. This includes confirmation of the configuration of the glycosidic linkages, and direct proof of the nature and ring form of dihydrostreptos...
Journal of the American Chemical Society, 2015
Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.