Gram-Scale Synthesis of the Fucose-Containing Fragments of Saccharomicins

Org Lett. 2024 Nov 1;26(43):9373-9377. doi: 10.1021/acs.orglett.4c03599. Epub 2024 Oct 17.

Abstract

A highly efficient synthetic route has been established for the gram-scale production of fucose-aglycon (Fuc-Agl) and fucose-saccharosamine (Fuc-Sac) fragments in saccharomicins A and B. The β-glycosidic bonds within these structural components were formed through successive rhodium(II) and Brønsted-acid-catalyzed glycosylation, utilizing a stable thioglycosyl donor. Subsequent steps involving the installation of protecting groups yielded highly functionalized synthetic fragments that are suitable for further assembly of saccharomicins.