4.4 Article

Stereoselective synthesis of safingol and its natural stereoisomer from D-glycals

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 32, Pages 4728-4730

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.05.112

Keywords

sphingolipid; safingol; glycals; Wittig reaction; catalytic hydrogenation

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Efficient and convenient syntheses of (2S,3S)-safingol and its natural (2S,3R)-isomer have been developed from 3,4,6-tri-O-benzyl glycals. The key step is the one-pot reduction of an azide, saturation of the double bonds and debenzylation under catalytic hydrogenation. (C) 2008 Elsevier Ltd. All rights reserved.

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