Stereoselective total syntheses of herbicidin C and aureonuclemycin through late-stage glycosylation.
Better late than never! Two herbicidins, members of an important family of nucleoside antibiotics, have been synthesized for the first time. The route integrates a stereoselective C-glycosylation with several reagent-controlled stereoselective transformations and a surprisingly facile and highly diastereoselective late-stage N-glycosylation.
Department of Chemistry, Ludwig-Maximilians-Universität München and Center of Integrated Protein Science, 81377 Munich, Germany.
Dominik
D
Hager
Peter
P
Mayer
Christian
C
Paulitz
Jörg
J
Tiebes
Dirk
D
Trauner
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002751:Chlortetracycline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006031:Glycosylation; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D006575:Heterocyclic Compounds, 3-Ring; D011684:Purine Nucleosides; C576019:herbicidin C; C013551:herbicidins; D000241:Adenosine; D002751:Chlortetracycline