Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 50, Pages 18068-18071Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502920
Keywords
alkyl shift; double Michael addition; hypervalent iodine; indoles; natural products
Categories
Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT)
- NSERC Vanier CGS program
- provincial government of Quebec (CCVC)
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A rapid route to 5,5- and 5,6-bicyclic systems is provided by an 1,3-alkyl-shift process mediated by a hyper-valent 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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