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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products

Author(s): C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide

Volume 11 , Issue 14 , 2004

Page: [1837 - 1872] Pages: 36

DOI: 10.2174/0929867043364900

Price: $65

Abstract

In the last two decades, the better understanding of the mechanistic aspects of the β-lactams biological activity and their inhibition, and the chemical exploitation of β-lactams as synthetic intermediates in organic chemistry, have experienced a continuous and somewhat complementary advance. A prerequisite for such a development has been the accessibility of enantiopure β-lactams. The latter are now routinely prepared most often through the ketene-imine cycloaddition reaction, also termed the Staudinger reaction. This review accounts for the recent progress made in the asymmetric synthesis of β-lactams (with special emphasis in the Staudinger reaction approach), as well as in their use as synthetic intermediates en route to natural products, including α- and β-amino acids and peptides derived therefrom.

Keywords: lactams, amino acids, peptides, imines, staudinger reaction, asymmetric synthesis


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