Synthesis and Absolute Configuration of Four Diastereomeric 1-(2-Furyl)-2-aminobutane-1,3-diols

Article abstract of DOI:10.1016/S0040-4020(01)90488-0

The synthesis of N-benzenesulfonyl-N,O-isopropylidene derivatives of (1R,2R,3S)-, (1S,2R,3S)-, (1R,2R,3R)- and (1S,2R,3R)-1-(2-furyl)-2-aminobutane-1,2-diols was accomplished by the addition of furyllithium to the similarly protected D-threoninal and D-allothreoninal, prepared in four steps from D-threonine and D-allothreonine, respectively.The configuration integrity of β-hydroxy-α-amino aldehydes as well as the structure and the stereochemistry of resultant aminodiols derivatives was established by 1H NMR spectroscopy and single-crystal X-ray analysis.