Effizient Synthesis of Deazaguanosine-Derived tRNA Nucleosides PreQ0, PreQ1 and Archaeosine Using the Turbo-Grignard Method

Eur. J.Org. Chem., 2010, 6517-6519 published on 22.10.2010
Eur. J. Org. Chem.
The natural products PreQ1, PreQ0, and archaeosine are deazaguanosine-derived natural products of immense biological importance. All three are critical components of tRNAs and, as such, are involved in decoding genetic information. We were able to consolidate and shorten the syntheses of all three compounds by using a novel Turbo-Grignard-based approach. The reported iodine/magnesium exchange followed by a Grignard reaction with the deazaguanosine skeleton showed a high tolerance towards important functional groups such as esters and amides.
TU München