The unnatural enantiomer of the alkaloid codonopsinine was prepared employing a suitably substituted alkoxyallene equipped with a D-fructose-derived auxiliary. The crucial lithiated 1-alkoxy-3-arylallene was generated in situ from easily available 1,2:4,5-di-O-isopropylidene-3-O-[3-(4-methoxyphenyl)-1,2-dien-1-yl]-β-D-fructopyranose and treated with an N-tosyl imine to afford a diastereomeric mixture of the corresponding allenyl adducts. Their cyclization with silver nitrate in acetonitrile in the presence of potassium carbonate furnished highly substituted 2,5-dihydropyrrole derivatives. After separation, straightforward synthetic operations, with highly diastereoselective hydroborations as key step, provided (+)-codonopsinine (≥95% ee) and one of its stereoisomers.