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[structures: see text] A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides.

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Synthesis of a Versatile (<i>S</i>)-3-(Hydroxymethyl)butane-1,2,4-triol Building Block and its Application for the Stereoselective Synthesis of <i>N</i>-Homoceramides

Synthesis of a Versatile (S)-3-(Hydroxymethyl)butane-1,2,4-triol Building Block and its Application for the Stereoselective Synthesis of N-Homoceramides