Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method

Abstract

Recent advances in the syntheses of enantiopure synthetic building blocks useful for non-protein amino acids, dipeptides, oligopeptides using solid state peptide synthesis, isoserines (norstatines), dipeptide isosteres [hydroxy(keto)ethylene, hydroxyethylamine, hydroxyethylene and dihydroxyethylene isosteres], taxoids, polyamines, poly(amino alcohol)s and poly(amino ether)s, and other biologically active compounds through applications of the b-lactam synthon method is reviewed.

A Versatile Synthesis of β‐Lactam‐Fused Oxacycles through the Palladium‐Catalyzed Chemo‐, Regio‐, and Diastereoselective Cyclization of Allenic Diols

“…[1] Moreover, the rigid structure and strain-driven reactivity make 2-azetidinone derivatives attractive as versatile intermediates in organic synthesis. [2] Over the past decades, vast efforts from chemists have been engaged by this area. Even so, complementary new approaches with high synthetic efficiency to build b-lactam-based structures remain highly desirable.…”

Conformational Analysis of β‐Lactam‐Containing Ferrocene Peptides

“…A variety of 3-amino-and 3-hydroxy-β-lactams with excellent enantiopurities can be obtained through chiral ester enolate/imine cyclocondensation. [4,6,10] Hydrolysis of 3-aminoand 3-hydroxy-β-lactams affords the corresponding α,β-diamino and α-hydroxy-β-amino acids. [11] This forms the foundation for applications of these β-lactams to asymmetric synthesis of nonprotein amino acids, peptides, dipeptide isosteres, and peptidomimetics that are not easily prepared by conventional methods.…”

“…[1,2] The potential of β-lactams to serve as intermediates for eventual access to α-and β-amino acid derived peptides has gained tremendous attention. [3][4][5][6] Enantiopure 3-amino- [7,8] and 3-hydroxy-β-lactams [9] are key intermediates for the synthesis of peptides and peptidomimetics. A variety of 3-amino-and 3-hydroxy-β-lactams with excellent enantiopurities can be obtained through chiral ester enolate/imine cyclocondensation.…”

β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

“…± Nonproteinogenic, enantiomerically pure 2,3-diamino acids are frequent components of antibiotics [1] [2], antifungal dipeptides [3], and other biologically active compounds [4] [5]. Enantiomerically pure 2,3-diamino and 2,3,4-triamino acids have been obtained by hydrolysis of appropriately substituted b-lactams [6] accessible by [2 2]-cycloaddition of either enantiomerically pure, glycine-derived ketenes to imines, or phthalimido ketenes to enantiomerically pure a-amino-imines ( [7] and refs. cit.…”