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Lessons and revelations from biomimetic syntheses

Nature Chemical Biology volume 7, pages 865–875 (2011)Cite this article

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Abstract

Biomimetic synthesis describes the field of organic chemistry that aims to emulate the natural, biosynthetic processes toward natural products. As well as providing insight into how molecules are formed in nature, the benefits of this approach to total synthesis are numerous and extend beyond the gains typical of traditional synthesis. For example, using biosynthetic proposals to design a synthetic route can highlight alternative methods to the desired target. The pursuit of biomimetic syntheses also promotes the development of new reactions to prove or disprove a biosynthetic proposal or to unravel mechanistic implications of a proposed biosynthesis and can lead to the identification of new natural products. Here we look at some recent compelling examples and examine how biomimetic synthesis has led to the discovery of new procedures and principles that would not have been found by other approaches.

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Figure 1: Seminal biomimetic syntheses.
Figure 2: Biomimetic two-phase synthesis of terpenoids.
Figure 3: Ladder polyethers.
Figure 4: Prenylated alkaloids.
Figure 5: Biosynthetic proposal and synthesis of exiguamine A and B.
Figure 6: Total synthesis of pyrrole-imidazole alkaloids.
Figure 7: Synthesis of the resveratrol polyphenols.
Figure 8: Total synthesis of berkelic acid (77).

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Acknowledgements

We thank J.M. Ready and U.K.Tambar (University of Texas Southwestern) for critical reading of this manuscript. We gratefully acknowledge financial support by the National Institutes of Health (CA 90349) and the Robert A. Welch Foundation (I-1422).

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  1. Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, Texas, USA

    Mina Razzak & Jef K De Brabander

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Razzak, M., De Brabander, J. Lessons and revelations from biomimetic syntheses. Nat Chem Biol 7, 865–875 (2011). https://doi.org/10.1038/nchembio.709

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