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Pure Appl. Chem., Vol. 72, No. 9, pp. 1763-1768, 2000.

 

 

Versatility of b-lactams in synthesis. Studies directed toward the synthesis of complex nucleoside antibiotics and some macrocyclic peptides*

Claudio Palomo**, Jesús M. Aizpurua, Iñaki Ganboa, and Mikel Oiarbide

Departamento de Química Orgánica, Facultad de Química, Universidad del País Vasco, Apdo 1072, 20080 San Sebastián, Spain

Abstract: The diastereoselective [2+2] cycloaddition of a-hydroxyketene equivalents with chiral a,w-oxyaldehyde-derived imines followed by the 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO)-promoted ring expansion of the resulting a-hydroxy b-lactam adducts provides an unconventional and short route to a-amino acid N-carboxy anhydrides (NCAs). The required enantiopure a,w-oxyaldehydes were obtained either from the chiral pool or through the Sharpless AD methodology. Following the present strategy, several nonproteinogenic NCAs were synthesized, which were further coupled with a-amino acid esters giving rise to key fragments of some nucleoside antibiotics and macrocyclic peptides.

*Lecture presented at the 13th International Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July 2000.
** Corresponding author

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