A general, iterative, and modular approach toward carbohydrate libraries based on ruthenium-catalyzed oxidative cyclizations

Research output: Contribution to journalResearch articleContributedpeer-review


  • Meike Niggemann - , University of Stuttgart (Author)
  • Andreas Jelonek - , University of Stuttgart (Author)
  • Nicole Biber - , University of Stuttgart (Author)
  • Margarita Wuchrer - , University of Stuttgart (Author)
  • Bernd Plietker - , University of Stuttgart (Author)


(Chemical Equation Presented) Carbohydrates are an omnipresent class of highly oxygenated natural products. Due to their wide spectra of biological activities, they have been in the center of synthetic organic chemistry for more than 130 years. During the past 50 years non-natural carbohydrates attracted the interest of various chemists in the fields of organic, biological, and medical chemistry. Especially desoxygenated sugars proved to be an important class of compounds. Up to date, most non-natural analogues are synthesized starting from natural, enantiomerically pure carbohydrates in multistep synthesis. In this report, we present a synthetic strategy that allows the selective modular synthesis of natural and non-natural carbohydrates within five synthetic steps starting from readily available starting materials. Due to a sequential introduction of O-or N-functionalities, a regioselective protection of each new functional group is possible. The key step in the carbohydrate synthesis is a RuO4-catalyzed oxidative eyclization via a pH-dependent dehydrogenation-dihydroxylation-cyclization or an oxidative fragmentation-cyclization, leading to highly substituted new carbohydrates, in which each functional group is orthogonally protected and accessible for further synthetic operations.


Original languageEnglish
Pages (from-to)7028-7036
Number of pages9
JournalJournal of organic chemistry
Issue number18
Publication statusPublished - 19 Sep 2008
Externally publishedYes

External IDs

PubMed 18707173


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