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

• Pramod R. Markad Navanath Kumbhar Dilip D. Dhavale Garware Research Centre, Department of Chemistry, Savitribai Phule Pune University (Formerly University of Pune), Pune-411007, India 10.3762/bjoc.12.165 Abstract The C8’-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D

• 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

• , antiviral, antibacterial and antifungal [2]. Peptidyl nucleosides in which the sugar part is in the furanose form are common, however, the sugar framework in the pyranose form, with a nucleobase and a peptide linker at either ends, are rare in nature. A few examples of this category are amipurimycin and