Total synthesis of 4-(D-alanylamino)-2-amino-2,3,4-trideoxy-DL-threo-pentose (3-deoxy-DL-prumycin)

Article abstract of DOI:10.1016/0008-6215(91)89015-8

3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-DL-pent-2-enopyranos-4-ulose (3) and reduction in situ of the adduct afforded the key i