Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues

Dominik Hager, Christian Paulitz, Jörg Tiebes, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)10784-10801
Number of pages18
JournalJournal of Organic Chemistry
Volume78
Issue number21
DOIs
StatePublished - Nov 1 2013

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Glycosylation
Biological Products
Nucleosides
Carbohydrates
Anti-Bacterial Agents
herbicidin C

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hager, D., Paulitz, C., Tiebes, J., Mayer, P., & Trauner, D. (2013). Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues. Journal of Organic Chemistry, 78(21), 10784-10801. https://doi.org/10.1021/jo401706r

Total synthesis of herbicidin C and aureonuclemycin : Impasses and new avenues. / Hager, Dominik; Paulitz, Christian; Tiebes, Jörg; Mayer, Peter; Trauner, Dirk.

In: Journal of Organic Chemistry, Vol. 78, No. 21, 01.11.2013, p. 10784-10801.

Research output: Contribution to journalArticle

Hager, D, Paulitz, C, Tiebes, J, Mayer, P & Trauner, D 2013, 'Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues', Journal of Organic Chemistry, vol. 78, no. 21, pp. 10784-10801. https://doi.org/10.1021/jo401706r
Hager, Dominik ; Paulitz, Christian ; Tiebes, Jörg ; Mayer, Peter ; Trauner, Dirk. / Total synthesis of herbicidin C and aureonuclemycin : Impasses and new avenues. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 21. pp. 10784-10801.
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