Formation of the Main Cores Present in Natural Products by Tandem Additions

Publisher: John Wiley & Sons Inc

E-ISSN: 1521-3765|21|50|18068-18071

ISSN: 0947-6539

Source: CHEMISTRY - A EUROPEAN JOURNAL, Vol.21, Iss.50, 2015-12, pp. : 18068-18071

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Abstract

AbstractA 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.