TY - JOUR
TI - Total synthesis of 4-(d-alanylamino)-2-amino-2,3,4-trideoxy-dl-threo-pentose (3-deoxy-dl-prumycin)
AU - Constantinou-Kokotou, V.
AU - Couladouros, E.A.
AU - Georgiadis, M.P.
AU - Kokotos, G.
AU - Georgiadis, T.M.
JO - Carbohydrate Research
PY - 1991
VL - 222
TODO - C
SP - 163-172
PB - 
SN - 0008-6215
TODO - 10.1016/0008-6215(91)89015-8
TODO - Drug Products - Antibiotics, Alanine;  Azido Group;  Prumycin, Carbohydrates, 3 deoxyprumycin;  antibiotic agent;  sugar;  unclassified drug, antifungal activity;  article;  drug structure;  drug synthesis;  nuclear magnetic resonance
TODO - 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 intermediates 5 and 6. Introduction of a second azido group with inversion of configuration at C-4 afforded intermediates 14 and 17, both of which had a threo configuration in regard to C-2 and C-4. Coupling with d-alanine and total deprotection yielded the title compound 1. © 1991.
ER -