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

Claudio Palomo; Jesús M. Aizpurua; Iñaki Ganboa; Mikel Oiarbide

doi:10.1351/pac200072091763

Publicly Available Published by De Gruyter January 1, 2009

Versatility of β-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

From the journal Pure and Applied Chemistry

https://doi.org/10.1351/pac200072091763

Abstract

The diastereoselective [2+2] cycloaddition of α-hydroxyketene equivalents with chiral α,ω-oxyaldehyde-derived imines followed by the 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO)-promoted ring expansion of the resulting α-hydroxy β-lactam adducts provides an unconventional and short route to α-amino acid N-carboxy anhydrides (NCAs). The required enantiopure α,ω-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 α-amino acid esters giving rise to key fragments of some nucleoside antibiotics and macrocyclic peptides.

Conference

International Conference on Organic Synthesis (ICOS-13), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 13th, Warsaw, Poland, 2000-07-01–2000-07-05

Published Online: 2009-01-01

Published in Print: 2000-01-01

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

Abstract

Conference

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