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Organocatalytic cascade reactions as a new tool in total synthesis

Nature Chemistry volume 2, pages 167–178 (2010)Cite this article

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Abstract

The total synthesis of natural products and biologically active compounds, such as pharmaceuticals and agrochemicals, has reached an extraordinary level of sophistication. We are, however, still far away from the 'ideal synthesis' and the state of the art is still frequently hampered by lengthy protecting-group strategies and costly purification procedures derived from the step-by-step protocols. In recent years several new criteria have been brought forward to solve these problems and to improve total synthesis: atom, step and redox economy or protecting-group-free synthesis. Over the past decade the research area of organocatalysis has rapidly grown to become a third pillar of asymmetric catalysis standing next to metal and biocatalysis, thus paving the way for a new and powerful strategy that can help to address these issues — organocatalytic cascade reactions. In this Review we present the first applications of such asymmetric organocascade reactions to the total synthesis of natural products.

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Figure 1: Organocatalysed cascade reactions.
Figure 2: First application of an organocatalysed cascade reaction in total synthesis.
Figure 3: Application of IM–EN sequences in total synthesis.
Figure 4: Application of EN–IM sequences in total synthesis.
Figure 5: Alternative EN and IM combinations in total synthesis.
Figure 6: Combination of metal- and organocatalysis in natural product synthesis.
Figure 7: Brønsted-acid-catalysed cascade reactions in natural product synthesis.
Figure 8: Applications of organocatalytic cascade reactions in the synthesis of pharmaceuticals.

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  1. Bayer CropScience AG, Alfred-Nobel-Str. 50, Monheim am Rhein, 40789, Germany

    Christoph Grondal

  2. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen, 52074, Germany

    Matthieu Jeanty & Dieter Enders

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Grondal, C., Jeanty, M. & Enders, D. Organocatalytic cascade reactions as a new tool in total synthesis. Nature Chem 2, 167–178 (2010). https://doi.org/10.1038/nchem.539

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