American Chemical Society
jo401706r_si_002.cif (240.75 kB)

Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New Avenues

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posted on 2013-11-01, 00:00 authored by Dominik Hager, Christian Paulitz, Jörg Tiebes, Peter Mayer, Dirk Trauner
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.