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An acid-catalyzed macrolactonization protocol.

Barry M Trost1, John D Chisholm

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.

Organic Letters
|October 12, 2002
PubMed
Summary
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A new base-free macrolactonization method efficiently produces macrolactones using vinyl esters and a ruthenium catalyst. This transesterification reaction offers a streamlined approach to synthesizing complex cyclic esters in good yields.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Macrolactonization is a key transformation in synthesizing natural products and pharmaceuticals.
  • Traditional methods often require harsh conditions or stoichiometric reagents.
  • Developing efficient and mild macrolactonization protocols remains an active area of research.

Purpose of the Study:

  • To develop a novel, base-free protocol for macrolactonization.
  • To explore the use of vinyl esters in ruthenium-catalyzed transesterification for macrolactone synthesis.
  • To achieve good yields of macrolactones under mild reaction conditions.

Main Methods:

  • The study employed a ruthenium catalyst, specifically [RuCl(2)(p-cymene)](2), for transesterification reactions.

Related Experiment Videos

  • Hydroxy acids were reacted with ethoxyacetylene in the presence of the catalyst and toluene.
  • Camphorsulfonic acid was used as an additive, with variations in addition order explored.

    • Main Results:

    • An efficient base-free macrolactonization protocol was successfully developed.
    • The reaction provided macrolactones in good yields.
    • The protocol utilizes vinyl esters in a transesterification process catalyzed by a ruthenium complex.

    Conclusions:

    • The developed protocol offers an efficient and base-free route to macrolactones.
    • This method represents a valuable addition to the synthetic chemist's toolkit for constructing cyclic esters.
    • The use of vinyl esters in ruthenium-catalyzed transesterification provides a mild alternative for macrolactonization.