Formation of the Main Cores Present in Natural Products by Tandem Additions |
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| Authors: | Dr Kimiaka C Guérard Vincent Hamel Dr Amandine Guérinot Cloé Bouchard‐Aubin Prof Sylvain Canesi |
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| Institution: | Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre‐Ville, Montréal, H3C 3P8, Québec (Canada) |
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| Abstract: | A rapid route to 5,5‐ and 5,6‐ bicyclic systems is provided by an 1,3‐alkyl‐shift process mediated by a hypervalent iodine reagent on aromatics. The structures obtained contain several unsaturations with different behaviors and reactivities. Such diversity allows further elaborations for the rapid formation of compact systems present in a variety of natural products. The potential for further transformations has been demonstrated by performing a double Michael addition. This cyclization process is regio‐ and stereoselective due to the presence of a former benzylic substituent. Furthermore, an extension of this approach has been accomplished on indole derivatives. |
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| Keywords: | alkyl shift double Michael addition hypervalent iodine indoles natural products |
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