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Synlett 1990; 1990(8): 433-440
DOI: 10.1055/s-1990-34718
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An Overview of the Total Synthesis of Pyrrolizidine Alkaloids via [4 + 1]Azide-Diene Annulation Methodology

Tomas Hudlicky* , Gustavo Seoane, John D. Price, Kumar G. Gadamasetti
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, USA
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Publication Date:
08 March 2002 (online)

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The design and the execution of a multi-generation approach to pyrrolizidine alkaloids is summarized. A historical perspective and the various solutions to the problems of regio-, stereo-, and enantiocontrol in the preparation of these ubiquitous natural products are provided. The details of the fourth generation approach based on the resolution of ß-oxo esters of prochiral alcohols by yeast are disclosed. As this particular approach did not (we think) lead to optically pure products, a fifth-generation solution to the problems that were encountered is proposed. 1. Introduction 2. Historical Perspective 3. Regiochemistry of the [4 + 1] Intramolecular Pyrroline Annulation 4. Stereochemical Control in the Pyrrolizidine Diol Series 5. Enantiocontrolled Approach to Pyrrolizidine Triols 6. Attempted Enantiocontrolled Approach to Pyrrolizidine Diols 7. Conclusion