Τίτλος:
Total synthesis of 4-(d-alanylamino)-2-amino-2,3,4-trideoxy-dl-threo-pentose (3-deoxy-dl-prumycin)
Γλώσσες Τεκμηρίου:
Αγγλικά
Περίληψη:
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.
Συγγραφείς:
Constantinou-Kokotou, V.
Couladouros, E.A.
Georgiadis, M.P.
Kokotos, G.
Georgiadis, T.M.
Περιοδικό:
Carbohydrate Research
Λέξεις-κλειδιά:
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
DOI:
10.1016/0008-6215(91)89015-8
