Synthesis of beta-lactam scaffolds for ditopic peptidomimetics.
[reaction: see text] Ring opening of alpha-substituted-alpha-methoxycarbonyl-N-nosylaziridines provides a practical access to enantiopure alpha,alpha'-disubstituted beta-lactam scaffolds, novel types of ditopic reverse turn surrogates. The procedure is general, short, and high yielding and starts from handy alpha-substituted serinates and alpha-amino acid derivatives.
Palomo
Claudio
C
Departamento de Química OrgAnica-I, Universidad del País Vasco, Facultad de Química, Apdo 1072, 20080 San SebastiAn, Spain.
Aizpurua
Jesus M
JM
Balentova
Eva
E
Jimenez
Azucena
A
Oyarbide
Joseba
J
Fratila
Raluca M
RM
Miranda
José Ignacio
JI
D001388:Aziridines / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry*
D001388:Aziridines; D010455:Peptides; D047090:beta-Lactams; C033132:aziridine