Synthesis of carbapyochelins via diastereoselective azidation of 5-(ethoxycarbonyl)methylproline derivatives.
Two configurationally stable carbon-based analogues of pyochelin have been prepared from Boc-pyroglutamic acid-tert-butyl ester in 11 and 13 steps. Introduction of the amino group was achieved by a highly diastereoselective electrophilic azidation reaction to afford novel bis-alpha-amino acid proline derivatives.
Liyanage
Wathsala
W
Department of Chemistry and Biochemistry, New Mexico State University, MSC3C, Las Cruces, New Mexico 88003, USA.
Weerasinghe
Laksiri
L
Strong
Roland K
RK
Del Valle
Juan R
JR
D001386:Azides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
C532793:5-(ethoxycarbonyl)methylproline; D001386:Azides; D010636:Phenols; D013844:Thiazoles; C025316:pyochelin; D011392:Proline