Journal
TETRAHEDRON LETTERS
Volume 41, Issue 52, Pages 10309-10312Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)01851-7
Keywords
asymmetric dihydroxylation; double stereodifferentiation; diastereoselective synthesis; sphingolipids; phytosphingosines
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The first diastereoselective synthesis of L-xylo-(2R,3S 4S)-C-18-phytosphingosine (1) has been achieved by double stereodifferentiation of enantiomerically enriched terminal olefin 14 using (DHQD(2))-PHAL ligand in an asymmetric dihydroxylation with a diastereomeric ratio of 83:17. This phytosphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate 21. (C) 2000 Elsevier Science Ltd. All rights reserved.
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