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Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165
Graphical Abstract
Figure 1: Antifungal antibiotic amipurimycin (1).
Scheme 1: Retrosynthesis of 2.
Scheme 2: Synthesis of 1,3-anhydrosugar 12 and 13.
Scheme 3: Formation of 2,7-dioxabicyclo[3.2.1]octane 12/13.
Figure 2: Conformational analysis of 13 and 14.
Figure 3: Geometrically optimized conformation of 12 and 13 respectively by DFT study.
Scheme 4: Glycosylation of 16.
Scheme 5: Glycosylation attempt by changing protections.
Scheme 6: Synthesis of nucleoside 2.