Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

• Pramod R. Markad,
• Navanath Kumbhar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

• the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipulation in 12 gave 21 that on stereoselective β-glycosylation afforded the pyranosyl thymine nucleoside 2 – a core of amipurimycin. Keywords: amipurimycin; 1,3-anhydrosugar; anti-fungal agent

• borate and NaN3 in DMF that afforded azido diol 10 and 11 as major isomers, respectively [18][19]. In the next step, individual hydrolysis of the 1,2-acetonide group in 10 and 11 using TFA–H2O (3:1) provided the corresponding 1,3-anhydrosugar 12 and 13 in good yield. The formation of 1,3-anhydrosugar 12

• this regard are in progress. Antifungal antibiotic amipurimycin (1). Conformational analysis of 13 and 14. Geometrically optimized conformation of 12 and 13 respectively by DFT study. Retrosynthesis of 2. Synthesis of 1,3-anhydrosugar 12 and 13. Formation of 2,7-dioxabicyclo[3.2.1]octane 12/13