Pyrrol-2-yl acyclo C-nucleosides

Coupling the Cl unprotected D-ribofuranose derivative 208 [95JAP(K)95/ 118268] or an analogous derivative of 2-deoxy-D-ribose (95S638) with 2-lithiopyrrole gave a mixture of the two stereoisomeric pyrrol-2-yl acyclo C-nucleosides 209 (Scheme 43). 

Synthesis of pyrrol-2-yl acyclo C-nucleosides by forming the pyrrole ring onto the alditolyl chain was reported in 1922, when Pauly and Ludwig prepared 3-ethoxycarbonyl-2-methyl-2-(D-ara6mo-tetritol-l-yl) pyrrole (211), the first example of these compounds, by reaction of 2-amino-2-deoxy-D-glucose (210) with ethyl acetoacetate (22ZPC170) (Scheme 44). Since then, Spanish chemists have pioneered the synthesis of these compounds using this route and extensively studied their properties and mecha-... 

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