Electrophilic aromatic prenylation via cascade cyclization

John G Kodet; Joseph J Topczewski; Kevyn D Gardner; David F Wiemer

doi:10.1016/j.tet.2013.08.056

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Electrophilic aromatic prenylation via cascade cyclization

Journal article

Peer reviewed

Electrophilic aromatic prenylation via cascade cyclization

John G Kodet, Joseph J Topczewski, Kevyn D Gardner and David F Wiemer

Tetrahedron, Vol.69(44), pp.9212-9218

11/04/2013

DOI: 10.1016/j.tet.2013.08.056

PMCID: PMC3940164

PMID: 24610962

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http://doi.org/10.1016/j.tet.2013.08.056View

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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 BF3·OEt2 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. [Display omitted]

Prenylation

Cyclization

Electrophilic aromatic substitution

Cationic

Tandem reactions

Details

Title: Subtitle: Electrophilic aromatic prenylation via cascade cyclization
Creators: John G Kodet
Joseph J Topczewski
Kevyn D Gardner
David F Wiemer
Resource Type: Journal article
Publication Details: Tetrahedron, Vol.69(44), pp.9212-9218
DOI: 10.1016/j.tet.2013.08.056
PMID: 24610962
PMCID: PMC3940164
NLM abbreviation: Tetrahedron
ISSN: 0040-4020
eISSN: 1464-5416
Publisher: Elsevier Ltd
Language: English
Date published: 11/04/2013
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985998202771

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