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Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of -xylo-[2R,3S,4S]-C18-phytosphingosine |
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| Authors: | Rodney A Fernandes Pradeep Kumar |
| Abstract: | The first diastereoselective synthesis of xylo-(2R,3S,4S)-C18-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. |
| Keywords: | asymmetric dihydroxylation double stereodifferentiation diastereoselective synthesis sphingolipids phytosphingosines |
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