The synthesis of taurospongin A has been achieved using, as a key step, a pi-allyltricarbonyliron lactone complex to control a highly stereoselective addition of a methyl group to a carbonyl unit located in the side chain of the complex.
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Synthesis of taurospongin A.
Org Lett
June 2010
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Two new routes to the C(1-10) carboxylic acid core of taurospongin A are presented. In the first route, overall asymmetric hydration of a C(2)-C(3) alkene is achieved by Sharpless AD and selective deoxygenation at C(2); in the second route, the C(3) stereogenic center is set by Tietze asymmetric allylation. A short synthesis of the C(1'-25') fatty acid combines with the product from the first route to complete the total synthesis of taurospongin A.
View Article and Find Full Text PDFCatalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones: formal asymmetric synthesis of taurospongin a.
J Am Chem Soc
May 2005
Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France.
Catalytic asymmetric vinylogous Mukaiyama reactions on ketones, leading to the formation of alpha,beta-unsaturated lactones with tertiary alcohols, have been described (11 examples, up to 93% ee). This methodology has been applied in a formal enantioselective synthesis of taurospongin A (12 steps, 6% overall yield).
View Article and Find Full Text PDFUse of pi-allyltricarbonyliron lactone complexes in the synthesis of taurospongin A: a potent inhibitor of DNA polymerase beta and HIV revers transcriptase.
Org Biomol Chem
May 2003
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK.
The total synthesis of taurospongin A by two new approaches has been achieved where pi-allyltricarbonyliron lactone complexes have been used to control highly stereoselective additions of the nucleophiles to a carbonyl unit located in the side chain of these complexes.
View Article and Find Full Text PDFAn enantioselective synthesis of the core unit of the non-nucleoside reverse transcriptase inhibitor taurospongin A.
Tetrahedron Asymmetry
March 2003
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA.
An enantioselective formal synthesis of taurospongin A has been achieved. The key steps involve chelation-controlled reductions of β-ketosulfoxide and β-hydroxy ketone intermediates and Sharpless asymmetric epoxidation to construct the tertiary alcohol stereoselectively.
View Article and Find Full Text PDFSynthesis of taurospongin A: a potent inhibitor of DNA polymerase and HIV reverse transcriptase, using pi-allyltricarbonyliron lactone complexes.
Chem Commun (Camb)
August 2002
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
The synthesis of taurospongin A has been achieved using, as a key step, a pi-allyltricarbonyliron lactone complex to control a highly stereoselective addition of a methyl group to a carbonyl unit located in the side chain of the complex.
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