A Facile Synthesis of Novel Acyclo-C-Nucleoside Analogues from L-Rhamnose via Variants of Bohlmann-Rahtz Reaction

[摘要]：

Synthesis of a series of novel acyclo-C-nucleoside analogues bearing substituted pyridines, dihydro-6H-quinolin-5-ones, dihydro-5H-cyclopentapyridin-5-one, tetrahydrocyclohepta[b]pyridine- 5-one, and azafluorinone has been achieved in very good yields, through CeCl3 center dot 7H(2)O-NaI-catalyzed one-pot condensation of a variant of the Bohlmann-Rahtz reaction using beta-enaminones derived from L-rhamnose, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. Ready availability of reactive beta-enaminones, use of a cerium catalyst, and shorter reaction times are the advantages of this protocol over previous methodology. A plausible mechanism invoking cerium-catalyzed sequential Michael addition-cyclode-hydration- elimination reactions is also presented.

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