Getting to the Core of Strychnos Alkaloids

  • Author: Claire D'Andola
  • Published Date: 15 December 2013
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Getting to the Core of <em>Strychnos</em> Alkaloids

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The syntheses of natural heterocyclic compounds and, in particular, indole alkaloids have been crucial drivers for the development of modern organic chemistry. Monoterpene indole alkaloids constitute a large and diverse class of natural products with all levels of molecular complexity and a wealth of biological activities. However, planning an appropriate, efficient, and atom-economic strategy for the total syntheses of these alkaloids is a challenging task, with the best strategies allowing access to a variety of different alkaloid structures with a minimum number of steps.

Hans-Ulrich Reissig and co-workers, Freie Universität Berlin, Germany, intrigued by the complex core structure of strychnine, have employed a samarium diiodide (SmI2)-induced cyclization-trapping method to easily construct highly functionalized dihydroindole derivatives.

These transformations led to the tetracyclic key building block suitable for the synthesis of the ABCEG rings of strychnine. An atom-economic synthesis was also developed employing a SmI2-induced cascade reaction of dimeric indolyl ketones to afford the ABGE core structure of strychnine in one step.

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH