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Beilstein J. Org. Chem. 2011, 7, 1228–1233, doi:10.3762/bjoc.7.143
Graphical Abstract
Scheme 1: Synthesis of potent antiviral and antitumor cyclonucleosides 5.
Figure 1: Lithiation of 2',3'-O-isopropylideneuridine (6).
Figure 2: Metalation of 5'-O-TMDMS protected nucleoside 10.
Figure 3: Lithiation/alkylation of 2',3',5'-tri-O-benzoyl-3,6-dimethyluridine (13) using LDA.
Scheme 2: Preparation of 2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-methyluridine (2).
Scheme 3: Lateral lithiation/alkylation of 6-methyluridine 2.
Figure 4: Bis-allylated products 20 and 21.