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Related Experiment Videos

Hydroxy-Directed, SmI(2)-Induced Conversion of Carbohydrates into Carbocycles.

Kan1, Nara, Ozawa

  • 1Department of Chemistry, Faculty of Science Hokkaido University Sapporo 060-0810 (Japan).

Angewandte Chemie (International Ed. in English)
|January 29, 2000
PubMed
Summary

Carbohydrates are transformed into polyoxygenated six-membered carbocycles using a novel hydroxy-directed coupling cyclization. This SmI(2)-induced reaction provides stereocontrolled synthesis of valuable cyclic compounds.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • Carbohydrates are abundant natural products with diverse structures.
  • Stereocontrolled synthesis of carbocyclic compounds is crucial in medicinal chemistry.
  • Existing methods for carbocycle synthesis from carbohydrates can be limited.

Purpose of the Study:

  • To develop a novel method for synthesizing polyoxygenated six-membered carbocycles from carbohydrates.
  • To achieve complete stereocontrol in the carbocyclization process.
  • To utilize samarium(II) iodide (SmI(2)) for hydroxy-directed coupling cyclization.

Main Methods:

  • Utilizing carbohydrate derivatives as starting materials.
  • Employing samarium(II) iodide (SmI(2)) for single-electron transfer.

Related Experiment Videos

  • Inducing hydroxy-directed coupling cyclization.
  • Generating a delta-hydroxy aldehyde intermediate in situ.

    • Main Results:

    • Successful derivation of polyoxygenated six-membered carbocycles from carbohydrates.
    • Complete stereocontrol was achieved throughout the synthesis.
    • High yields of target compounds, such as cis-1,3-cyclohexanediol, were obtained.
    • The reaction mechanism involves single-electron transfer from SmI(2) to a formyl group.

    Conclusions:

    • The SmI(2)-induced hydroxy-directed coupling cyclization is an effective method for stereocontrolled carbocycle synthesis from carbohydrates.
    • This approach offers a new route to complex cyclic structures from readily available starting materials.
    • The methodology demonstrates the utility of SmI(2) in mediating challenging organic transformations.