A convergent and stereoselective synthesis of the glycolipid components phthioceranic acid and hydroxyphthioceranic acid
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 2297501
Author(s) Pischl, Matthias C.; Weise, Christian F.; Müller, Marc-André; Pfaltz, Andreas; Schneider, Christoph
Author(s) at UniBasel Pfaltz, Andreas
Müller, Marc-André
Year 2013
Title A convergent and stereoselective synthesis of the glycolipid components phthioceranic acid and hydroxyphthioceranic acid
Journal Angewandte Chemie International Edition
Volume 52
Number 34
Pages / Article-Number 8968-8972
Keywords asymmetric synthesis, hydrogenation, Mycobacterium tuberculosis, natural product synthesis, polydeoxypropionates
Abstract Simply convergent: The polydeoxypropionates 1 and 2 are important constituents of the cell wall of Mycobacterium tuberculosis. Key steps in their total synthesis include two Suzuki–Miyaura cross-coupling reactions and two highly diastereoselective iridium-catalyzed hydrogenations. The trideoxypropionates employed as central building blocks were prepared by sequential oxy-Cope rearrangement, hydrogenation, and enolate methylation.
Publisher Wiley
ISSN/ISBN 1433-7851 ; 1521-3773
edoc-URL http://edoc.unibas.ch/dok/A6212004
Full Text on edoc No
Digital Object Identifier DOI 10.1002/anie.201303776
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/23843294
ISI-Number WOS:000323102100030
Document type (ISI) Article
 
   

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