SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 4 DIASTEREOISOMERIC 1-(2-FURYL)-2-AMINOBUTANE-1,3-DIOLS

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-amin obutane-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-threoinine and D-allothreonine, respectively. The c onfiguration integrity of a beta-hydroxy-alpha-amino aldehydes as well as the structure and the stereochemistry of resultant aminodiols deri vatives was established by H-1 NMR spectroscopy and single-crystal X-r ay analysis.