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Synthesis of bicyclo 3.1.0 hexanes functionalized at the tip of the cyclopropane ring. Application to the synthesis of carbocyclic nucleosides

  1. Author:
    Comin, M. J.
    Parrish, D. A.
    Deschamps, J. R.
    Marquez, V. E.

  2. Author Address

    NCI, Ctr Canc Res, Med Chem Lab, NIH, Frederick, MD 21702 USA. USN, Res Lab, Washington, DC 20375 USA.;Marquez, VE, NCI, Ctr Canc Res, Med Chem Lab, NIH, Frederick, MD 21702 USA.;marquezv@mail.nih.gov
    1. Year: 2006
    2. Date: Feb
  2. Journal: Organic Letters
    1. 8
    2. 4
    3. Pages: 705-708
  4. Type of Article: Article
  5. ISSN: 1523-7060
  1. Abstract:

    A general synthetic strategy for the preparation of functionalized bicyclo[3.1.0]hexanes is described. The new approach employs a cross metathesis step designed to functionalize the appropriate terminal olefin of the bicyclo[3.1.0]hexane precursor and a carbene-mediated intramolecular cyclopropanation reaction on the corresponding diazo intermediate. This combined methodology allowed the diastereoselective introduction of chemically diverse substituents at the tip of the cyclopropane group, except in cases where the substituents consisted of electron-withdrawing groups where a competing [3 + 2] cycloaddition predominated.

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External Sources

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  2. DOI: 10.1021/ol052886n
  3. View record in Web of Science®
  4. WOS: 000235534800040

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