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Formation of the Main Cores Present in Natural Products by Tandem Additions
Author(s) -
Guérard Kimiaka C.,
Hamel Vincent,
Guérinot Amandine,
BouchardAubin Cloé,
Canesi Sylvain
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502920
Subject(s) - hypervalent molecule , reagent , chemistry , stereoselectivity , substituent , indole test , tandem , bicyclic molecule , alkyl , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , materials science , composite material
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.