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

V Constantinou-Kokotou, EA Couladouros…

Index: Constantinou-Kokotou; Couladouros; Georgiadis; Kokotos Carbohydrate Research, 1991 , vol. 222, p. 163 - 172

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Citation Number: 10

Abstract

Abstract 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. ...

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