SYNTHESES OF HYPERMODIFIED NUCLEOSIDE Q, AND ITS BIOSYNTHETIC PRECURSORS PREQ0 AND PREQ1

Article abstract of DOI:10.1016/S0040-4020(01)87419-6

The nucleoside Q (1) and its biosynthetic precursors, preQ₀ (2) and preQ₁ (3) were synthesized from the key intermediate, 6-bromo-2-diacetylamino-3,4-dihydro-3-methoxymethyl-5-methyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one (6) by conversion of the methyl group on the base to 3S,4R,5S-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl, cyano, and aminomethyl groups, respectively.