Linked Life Data

17217286

Source:http://linkedlifedata.com/resource/pubmed/id/17217286

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
2007-1-12
pubmed:abstractText
Conditions were found for the successful Effenberger alpha,alpha'-annulation of 3,3-dimethyl-2,4,6-triprenyl cyclohexanone silyl enol ethers with malonyl chloride to give the corresponding bicyclo[3.3.1]nonane-trione in 35% yield, this result allowing a short synthesis of (+/-)-clusianone. An isomeric rearranged bicyclo[3.3.1]nonane-trione was also isolated in 25% yield, and changing the Lewis acid resulted in formation of a lavandulyl-substituted phloroglucinol derivative in 38% yield. The mechanism of formation of these two last products mimics the biogenetic pathway to PPAPs. [reaction: see text].
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
1523-7060
pubmed:author
pubmed:issnType
Print
pubmed:day
18
pubmed:volume
9
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
287-9
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Alpha,alpha'-annulation of 2,6-prenyl-substituted cyclohexanone derivatives with malonyl chloride: application to a short synthesis of (+/-)-clusianone. Formation and rearrangement of a biogenetic-like intermediate.
pubmed:affiliation
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
pubmed:publicationType
Journal Article