A stereoselective and efficient route to (3S, 4R, 5S)-(+)-4,5- dihydroxycyclopent-1-en-3-ylamine: The side chain of the hypermodified nucleoside Q

Article abstract of DOI:10.1016/S0040-4039(98)01738-9

A stereoselective and high yielding route is described to a suitably protected derivative of (3S, 4R, 5S)-(+)-3-amino-4,5-dihydroxycyclopent-1- ene, the side chain moiety of queuosine. The synthetic route comprises a ring-closing metathesis (RCM) of a mannofuranose-derived diene followed by Overman rearrangement.