Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes: incorporation of polyhydroxylated carbocyclic beta-amino acids into peptides.
A promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties. [reaction: see text]
Soengas
Raquel G
RG
Departamento de Química Orgánica, Universidade de Santiago, 15782 Santiago de Compostela, Spain.
Estévez
Juan C
JC
Estévez
Ramón J
RJ
D000146:Acids, Carbocyclic / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006536:Heptanes / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000146:Acids, Carbocyclic; D000588:Amines; D000596:Amino Acids; D003517:Cyclopentanes; D006536:Heptanes; D006601:Hexoses; D010455:Peptides