Linked Life Data

19199796

Source:http://linkedlifedata.com/resource/pubmed/id/19199796

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
5
pubmed:dateCreated
2010-6-3
pubmed:abstractText
An oxidative Friedel-Crafts reaction involving different aromatic compounds mediated by a hypervalent iodine reagent has been performed, using polysubstituted phenols. The strategy fits within the concept of "aromatic ring umpolung", which opens up novel opportunities in chemical synthesis. The reaction takes place in useful yields, and allows rapid access to highly functionalized compounds containing a dienone, a quaternary carbon center, and an aromatic ring. The product's skeleton is present in numerous natural products. As an illustration of the potential of this transformation, total syntheses of compounds belonging to the Amaryllidaceae alkaloids family such as O-methyljoubertiamine, mesembrine, and its natural derivative the dihydro-O-methylsceletenone have been achieved in eight/nine steps. The synthetic route to these molecules features a novel and efficient transformation on the basis of a Fukuyama and Michael-retro-Michael tandem process to produce the required nitrogen-containing ring system.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Mar
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
6
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2039-45
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Oxidative Friedel-Crafts reaction and its application to the total syntheses of Amaryllidaceae alkaloids.
pubmed:affiliation
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succursale Centre-Ville, Montréal, H3C 3P8, Québec, Canada.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't