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Beilstein J. Org. Chem. 2019, 15, 801–810, doi:10.3762/bjoc.15.77
Graphical Abstract
Figure 1: Adefovir (1) and its prodrug 2.
Scheme 1: Literature syntheses of 1.
Figure 2: Retrosynthetic analysis of 6 to synthons 9 and 10.
Scheme 2: Forward synthesis of 6 from 9 and 10.
Figure 3: Retrosynthesis of 6 to synthons 14 and 3.
Scheme 3: Application of related alkyl iodide 15 [52].
Scheme 4: Synthesis of 6 and 20 via iodide 14.
Scheme 5: Synthesis of phosphonate 6 using novel salt 21.
Scheme 6: Application of iodide 14 in the synthesis of adefovir analogues.
Figure 4: HMBC spectrum confirms N7-selectivity for the major product 29.
Scheme 7: Attempted synthesis of adefovir dipivoxil (2) exploiting phosphonate 33.