1391973-90-2Relevant academic research and scientific papers
Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues
Hager, Dominik,Paulitz, Christian,Tiebes, Joerg,Mayer, Peter,Trauner, Dirk
, p. 10784 - 10801 (2013/11/19)
The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful strategy benefits from a variety of reagent-controlled stereoselective transformations, including a surprisingly facile and highly diastereoselective N-glycosylation process. The presented work also describes new building blocks that might find further application in carbohydrate chemistry.
Stereoselective total syntheses of herbicidin C and aureonuclemycin through late-stage glycosylation
Hager, Dominik,Mayer, Peter,Paulitz, Christian,Tiebes, J?rg,Trauner, Dirk
, p. 6525 - 6528 (2012/07/27)
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. Copyright
