Sydnone Ribosides as a Platform for the Synthesis of Pyrazole C-Nucleosides: A Unified Synthesis of Formycin B and Pyrazofurin

Org Lett. 2020 Dec 4;22(23):9287-9291. doi: 10.1021/acs.orglett.0c03523. Epub 2020 Nov 19.

Abstract

The C-nucleoside natural products formycin B and pyrazofurin were synthesized in seven steps employing a sydnone riboside as common intermediate. Sydnone ribosides were synthesized via a direct Lewis acid catalyzed dehydrative glycosylation reaction. We demonstrated that these can be used for the diversity-oriented synthesis of pyrazole C-nucleoside analogues via thermal 1,3-dipolar cycloaddition reactions with various alkynes, giving access to the pyrazole C-nucleoside natural products, as well as opening new avenues for exploring nucleoside chemical space.

Publication types

  • Research Support, Non-U.S. Gov't