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Complex Natural Products Derived from Pyrogallols

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Progress in the Chemistry of Organic Natural Products 118

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 118))

Abstract

Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.

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Acknowledgements

Alexander J.E. Novak thanks New York University for a MacCracken and a Ted Keusseff fellowship. Dirk Trauner would like to thank the U.S. National Institutes of Health for financial support (grant R01GM126228).

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Authors and Affiliations

  1. Department of Chemistry, New York University, 31 Washington Place, New York, NY, 10003, USA

    Alexander J. E. Novak & Dirk Trauner

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  1. Alexander J. E. Novak
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  2. Dirk Trauner
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Correspondence to Dirk Trauner .

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Editors and Affiliations

  1. College of Pharmacy, Ohio State University, Columbus, OH, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University, Linz, Austria

    Heinz Falk

  3. School of Pharmacy, University of East Anglia, Norwich, UK

    Simon Gibbons

  4. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

    Yoshinori Asakawa

  5. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, China

    Ji-Kai Liu

  6. Department of Pharmaceutical Sciences, University of Vienna, Vienna, Wien, Austria

    Verena M. Dirsch

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Novak, A.J.E., Trauner, D. (2022). Complex Natural Products Derived from Pyrogallols. In: Kinghorn, A.D., Falk, H., Gibbons, S., Asakawa, Y., Liu, JK., Dirsch, V.M. (eds) Progress in the Chemistry of Organic Natural Products 118. Progress in the Chemistry of Organic Natural Products, vol 118. Springer, Cham. https://doi.org/10.1007/978-3-030-92030-2_1

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