A practical synthesis of D-erythro-Sphingosine using a cross-metathesis approach

ORGN 108

Staffan Torssell and Peter Somfai. Department of Chemistry, Organic Chemistry, Royal Institute of Technology, Teknikringen 56, 100 44 Stockholm, Sweden
Sphingolipids are constituents of cell membranes in all eukaryotic cells and the recent discovery of their biologically active metabolites e.g. sphingosine, ceramide and lysosphingolipids has generated interest in the physiological role of these molecules.

Starting from vinylepoxide 3, a short and practical synthesis of D-erythro-Sphingosine is described. The key transformations are a regioselective opening of the vinylepoxide and an E-selective cross-metathesis, affording the target molecule in 5 steps and 51% overall yield. The cross-metathesis was accomplished using either Grubbs’ second generation catalyst with a stoichiometric amount of Ti(OiPr)4 or with the newly developed 3-bromopyridine Ru-catalyst.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004