Stereoselective Synthesis of Unnatural (2S,3S)-6-Hydroxy-4-Sphingenine-Containing Sphingolipids.
(2019) Stereoselective Synthesis of Unnatural (2S,3S)-6-Hydroxy-4-Sphingenine-Containing Sphingolipids. Org Biomol Chem 17(29), 6964-6969.
6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using a underexplored hydrozirconation-transmetalation reaction and an unusal three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6‑hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labled derivative suitable for future biological studies.
doi: 10.1039/C9OB00990F PMID: 31134244