Linked Life Data

19852460

Source:http://linkedlifedata.com/resource/pubmed/id/19852460

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
22
pubmed:dateCreated
2009-11-13
pubmed:abstractText
We have developed a strategy for constructing nitrogen heterocycles by photoinduced PhSe group transfer radical cyclization. trans-Alpha,beta-disubstituted gamma-butyrolactams (2-pyrrolidinones) were prepared in good yields (38-73%) with high regioselectivity and stereoselectivity from N-alkenyl alpha-PhSe beta-keto amides. Reaction outcomes were modulated by the steric effect of the substituents on the nitrogen atom of the cyclization precursors and the stereoelectronic effect of the substrates. Diphenyldiselenide, as an additive, was found to promote ring closure. The advantage of this strategy in natural product synthesis is demonstrated by a formal synthesis of (+/-)-isocynometrine.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
20
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
8610-5
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Synthesis of gamma-butyrolactams by photoinduced PhSe group transfer radical cyclization and formal synthesis of (+/-)-isocynometrine with diphenyldiselenide as promoter.
pubmed:affiliation
Department of Chemistry, Fudan University, Shanghai 200433, China. yangdan@hku.hk
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't