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Synthesis 2012; 44(15): 2340-2346
DOI: 10.1055/s-0031-1289813
DOI: 10.1055/s-0031-1289813
paper
Total Synthesis of d-lyxo-Phytosphingosine and Formal Synthesis of Pachastrissamine via a Chiral 1,3-Oxazine
Further Information
Publication History
Received: 27 March 2012
Accepted after revision: 14 May 2012
Publication Date:
26 June 2012 (online)
Abstract
Concise and efficient syntheses of d-lyxo-phytosphingosine and pachastrissamine were achieved utilizing a chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and intermolecular olefin cross-metathesis.
Key words
palladium catalysis - sphingolipids - stereoselective synthesis - cross-coupling - natural productsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
Primary Data
- for this article are available online and can be cited using the following DOI: 10.4125/pd0031th. The primary data set includes FIDs and associated files for the 1H and 13C NMR spectra as well as NOE experiments.
- Primary Data
-
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For recent reviews of phytosphingosines, see:
For more recent syntheses of phytosphingosines, see:
For recent syntheses of d -lyxo-phytosphingosine, see:
For reviews on pachastrissamine syntheses, see:
For recent syntheses of pachastrissamine, see: