Logo der Universität Basel

Research Database / FORSCHUNGSDATENBANK 
PRINTDOC
 
Publication 2815366 | Verified
 

Data Entry: Please note that the research database will be replaced by UNIverse by the end of October 2023. Please enter your data into the system https://universe-intern.unibas.ch. Thanks

Login for users with Unibas email account...

Login for registered users without Unibas email account...

 
A Highly Stereoselective and Flexible Strategy for the Convergent Synthesis of Long-Chain Polydeoxypropionates: Application towards the Synthesis of the Glycolipid Membrane Components Hydroxyphthioceranic and Phthioceranic Acid
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 2815366
Author(s) Pischl, Matthias C.; Weise, Christian F.; Haseloff, Stefan; Mueller, Marc-Andre; Pfaltz, Andreas; Schneider, Christoph
Author(s) at UniBasel Pfaltz, Andreas
Year 2014
Title A Highly Stereoselective and Flexible Strategy for the Convergent Synthesis of Long-Chain Polydeoxypropionates: Application towards the Synthesis of the Glycolipid Membrane Components Hydroxyphthioceranic and Phthioceranic Acid
Journal Chemistry - A European Journal
Volume 20
Number 52
Pages / Article-Number 17360-17374
Abstract A highly stereocontrolled and flexible access to biologically relevant polydeoxypropionates in optically pure form has been developed. Taking advantage of our previously established strategy for the asymmetric and stereodivergent synthesis of trideoxypropionate building blocks, we have now been able to assemble large polydeoxypropionate chains with defined configuration in a highly convergent manner. Central steps of this approach include two Suzuki-Miyaura cross-coupling reactions with subsequent highly diastereoselective hydrogenations to join three advanced synthetic intermediates in excellent yield and with full stereochemical control. We have applied this strategy successfully towards the asymmetric synthesis of glycolipid membrane components phthioceranic acid and hydroxyphthioceranic acid, the latter of which was synthesized on a half-gram scale.
Publisher Wiley
ISSN/ISBN 0947-6539 ; 1521-3765
edoc-URL http://edoc.unibas.ch/50845/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/chem.201404034
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/25351748
ISI-Number WOS:000346468000016
Document type (ISI) Article
 
   

MCSS v5.8 PRO. 0.357 sec, queries - 0.000 sec ©Universität Basel  |  Impressum   |    
19/04/2024