Linked Life Data

17253824

Source:http://linkedlifedata.com/resource/pubmed/id/17253824

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
2007-1-26
pubmed:abstractText
Chemoselective SN2' condensation of primary enolates of alkyl methyl ketones 2a-e with dimethyl bromomethylfumarate (1) followed by highly diastereoselective NaBH4 reduction of the ketone function in the formed ketodiesters 3a-e and the regioselective in situ lactonization of the unisolable intermediates 4a-e exclusively furnished the cis-3,5-disubstituted gamma-butyrolactones (+/-)-5a-e in very good yields. Similarly, the face-selective coupling reaction of cyclohexanone enolate with 1 to form a mixture of diastereomers in an 8:2 ratio followed by a highly selective reductive cyclization of 9 plus 10 exclusively provided the cis-octahydrobenzofuran (+/-)-12 in 70% overall yield.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
2
pubmed:volume
72
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1009-12
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Facile chemo-, regio-, and diastereoselective approach to cis-3,5-disubstituted gamma-butyrolactones and fused gamma-butyrolactones.
pubmed:affiliation
Division of Organic Chemistry (Synthesis) and Centre for Material Characterization, National Chemical Laboratory, Pune 411 008, India.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't