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Electrophilic aromatic prenylation via cascade cyclization
- Source :
- Tetrahedron. 69(44)
- Publication Year :
- 2014
-
Abstract
- To gain access to prenylated hexahydroxanthenes, tandem cascade cyclization–electrophilic aromatic substitution reactions have been studied on substrates bearing allylic and propargylic substituents. Both BF 3 ·OEt 2 and TMSOTf can be used to initiate this reaction sequence, resulting in different ratios of the C-2 and C-6 substitution products. Even though allylic transposition is observed in some cases, the results of a crossover experiment are consistent with an intramolecular reaction sequence. Taken together, these studies now allow preparation of either the C-2 or C-6 prenylated hexahydroxanthene products.
Details
- ISSN :
- 00404020
- Volume :
- 69
- Issue :
- 44
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi.dedup.....48ef986eac2d1315090b012b79cf6182