Straightforward stereoselective access to cyclic peptidomimetics.
The preparation of cyclic dipeptide mimetics from chiral imino lactones derived from (R)-phenylglycinol is described. Key steps of the synthetic route included the fully stereoselective construction of a quaternary center, the formation of six-, seven-, or eight-membered lactams by means of an RCM cyclization, and the introduction of a new amino group within the lactam ring. The synthesis of a tripeptide mimetic is also reported.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Mateu
Natalia
N
Albert
Laia
L
Aceña
José Luis
JL
D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D018716:Molecular Mimicry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004151:Dipeptides; D004983:Ethanolamines; D007783:Lactones; D010456:Peptides, Cyclic; C005332:N-phenylethanolamine; D005998:Glycine