A new approach to the synthesis of sphingoid bases has been developed. The strategy is based on Sonogashira coupling of a chiral acetylenic carbamate that can be prepared in enantiomerically enriched form from 2,3-epoxy-4-pentyn-1-ol, which is readily accessible by Sharpless asymmetric epoxidation. Several N-Boc-sphingadienines and aromatic ceramide analogs have been synthesized.
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