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Synthesis and biological activities of 4-(d-alanylamino)-2-amino-2,3,4-trideoxy-l-threo-pentose (3-deoxyprumycin)

✍ Scribed by Hironobu Hashimoto; Koichi Araki; Ken-ichi Miyazawa; Juji Yoshimura


Book ID
108307776
Publisher
Elsevier Science
Year
1982
Tongue
English
Weight
779 KB
Volume
99
Category
Article
ISSN
0008-6215

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Total synthesis of 4-(d-alanylamino)-2-a
✍ Violetta Constantinou-Kokotou; Elias A. Couladouros; Minas P. Georgiadis; George πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 English βš– 726 KB

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-oqent-2-enopyranos~ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second ax