Amaya Berecibar

Cycloaddition Reactions of Carbohydrate Derivatives. Part III. A New Route to Swainsonine Analogs.

Abstract Swainsonine analogs 10 and 12 have been synthesized from D- and L-arabinose, respectively, using cyclocondensation of azomethines with Danishefskys diene followed by stereoselective carbonyl and double bond reduction of the resulting pyridones, chain shortening and ring closure by reductive amination.

Cycloaddition reactions of carbohydrate derivatives. Part VI. Quinolizidine analogs of castanospermine

Abstract Octahydroquinolizine-1,2,3,8-tetraols 12, 16 and 23, analogs of castanospermine, were synthesized from D-glucose, L-arabinose and D-mannose, respectively, using hetero-Diels-Alder reactions of sugar-derived azomethines as the key step.

Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs

Diastereoselective hetero Diels-Alder reactions of sugar derived azomethines 4a–4g have been used for the construction of chiral piperidones 6 and 7. Configuration of the major products was 6,1′-threo in every case. The enone system of 6 and 7 was reduced diastereoselectively and subsequently swainsonine-analog hydroxyindolizidines 28–32 were prepared by an intramolecular reductive amination.