Linked Life Data

17295364

Source:http://linkedlifedata.com/resource/pubmed/id/17295364

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
14
pubmed:dateCreated
2007-5-24
pubmed:abstractText
A convergent asymmetric total synthesis of pironetin (1), a polyketide with immunosuppressive, antitumor, and plant-growth regulating activities is described. The synthesis was realized by coupling between the C(8)-C(14) 2 and C(7)-C(2) 15 fragments, respectively, by using a Mukaiyama-aldol reaction. The stereogenic centers of each fragment were generated by employing the SAMP/RAMP hydrazone (SAMP=(S)-1-amino-2-methoxymethylpyrrolidine, RAMP=(R)-1-amino-2-methoxymethylpyrrolidine) methodology as a key step. An asymmetric alpha-alkylation of diethyl ketone permitted the introduction of the C(10) stereogenic center of 2, whereas the stereocenters C(4) and C(5) of 15 were installed by an asymmetric aldol reaction. Finally, the formation of the alpha,beta-unsaturated delta-lactone was achieved by ring-closing metathesis in the presence of catalytic amounts of titanium tetraisopropoxide.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
0947-6539
pubmed:author
pubmed:issnType
Print
pubmed:volume
13
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3942-9
pubmed:dateRevised
2009-8-4
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Asymmetric total synthesis of (-)-pironetin employing the SAMP/RAMP hydrazone methodology.
pubmed:affiliation
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany. Enders@RWTH-Aachen.de
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't