2′,3′-Dideoxyadenosine Analogs of the Nucleoside Antibiotics Tubercidin, Toyocamycin and Sangivamycin

Abstract

Application of previously described methodologies, for the synthesis of 2′,3′-dideoxy-2′,3′-didehydro nucleosides from the parent ribonucleosides, to the antibiotics tubercidin (1), toyocamycin (6) and sangivamycin (10) has provided the corresponding 2′,3′-unsaturated nucleosides 4, 9, and 13. A reduction of the 2′,3′-unsaturated moiety has afforded the 2′,3′-dideoxynucleoside antibiotics 5, 14, and 15.