Linked Life Data

21058386

Source:http://linkedlifedata.com/resource/pubmed/id/21058386

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2010-12-28
pubmed:abstractText
A detailed description of our second-generation total synthesis of salinosporamide A is presented. Three contiguous stereocenters in the ?-lactam structure seen in the natural product were established by stereoselective functionalization of a D-arabinose scaffold, including an Overman rearrangement to generate a highly congested tetrasubstituted carbon center. One of the definitive reactions in the synthesis was a Lewis acid mediated skeletal rearrangement of a pyranose structure, which enabled the practical conversion of the carbohydrate scaffold to the ?-lactam structure embedded in salinosporamide A. The use of a benzyl ester as a protective group for a sterically hindered carboxylic acid led to a one-pot global deprotection at the end of the synthesis.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
1861-471X
pubmed:author
pubmed:issnType
Electronic
pubmed:day
3
pubmed:volume
6
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
209-19
pubmed:dateRevised
2011-9-12
pubmed:meshHeading
pubmed:year
2011
pubmed:articleTitle
Total synthesis of (-)-salinosporamide A.
pubmed:affiliation
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't