rdf:type |
|
lifeskim:mentions |
|
pubmed:issue |
21
|
pubmed:dateCreated |
2005-10-7
|
pubmed:abstractText |
[structure: see text] The design, total synthesis, and biological evaluation of two C13-C14-cyclopropyl analogues [(+)-1 and (+)-2] of (+)-discodermolide have been achieved. Key features of the syntheses include highly stereoselective, hydroxyl-directed cyclopropanations of vinyl iodides and higher order cuprate-mediated cross-coupling reactions between cyclopropyl iodides and alkyl iodides. Biological evaluation revealed that neither orientation of the cyclopropyl methylene completely substitutes for the C14 methyl found in (+)-discodermolide (3).
|
pubmed:grant |
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Oct
|
pubmed:issn |
1523-7060
|
pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:day |
13
|
pubmed:volume |
7
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
4613-6
|
pubmed:dateRevised |
2007-11-14
|
pubmed:meshHeading |
pubmed-meshheading:16209492-Alkanes,
pubmed-meshheading:16209492-Antineoplastic Agents,
pubmed-meshheading:16209492-Carbamates,
pubmed-meshheading:16209492-Cell Survival,
pubmed-meshheading:16209492-Cyclopropanes,
pubmed-meshheading:16209492-Drug Design,
pubmed-meshheading:16209492-Humans,
pubmed-meshheading:16209492-Lactones,
pubmed-meshheading:16209492-Molecular Structure,
pubmed-meshheading:16209492-Pyrones,
pubmed-meshheading:16209492-Stereoisomerism,
pubmed-meshheading:16209492-Structure-Activity Relationship
|
pubmed:year |
2005
|
pubmed:articleTitle |
Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues of (+)-discodermolide.
|
pubmed:affiliation |
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
|
pubmed:publicationType |
Journal Article,
Research Support, N.I.H., Extramural
|