New route to N-alkylated trans-pyrrolidine diols from 2,2,3,3- tetramethoxybutane-protected dimethyl tartrate

Article abstract of DOI:10.1080/00397910801916520

A short synthesis of some trans-pyrrolidine diols is described starting from (2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester 3. The key step was the occurrence of a tandem azide reduction/cyclization sequence on mono-azide intermediate 6 upon catalytic hydrogenation. This method afforded both (3R,4R)-(+)-1-benzyl-3,4- pyrrolidinediol 9a and (3R,4R)-(+)-1-allyl-3,4-pyrrolidinediol 9b starting from 3. Cytotoxicity tests were performed on compounds 9a and 9b using the brine shrimp bioassay, but each showed no activity, as were anti-oxidant tests using the stable free radical diphenylpicrylhydrazyl (DPPH). Copyright Taylor & Francis Group, LLC.