A second synthesis of D-apio-beta-D-furanosyl maleimide as a structural analogue of showdomycin

摘要

Apioshowdomycin (3-(D-apio-4-D-furanosyl)-1H-pyrrole-2,5-dione, 2) has been pre pared as an analogue of the C-nucleoside showdomycin (1) in seven steps. starting from 2,3-O-isopropylidene-D-apio-D-furanose (8). The key step is the addition of a radical generated from apiosyl bromide 5b to (E)-methyl 3-cyanoacrylate (4).