Asymmetric hetero Diels-Alder as an access to carbacephams.
A short and efficient asymmetric synthesis of the (6R,7S)-7-tert-butoxycarbonylamino-2-ketocarbacepham is described. The key step involves the hetero Diels-Alder reaction of the benzylimine derived from the enantiomer of Garner's aldehyde with Danishefsky's diene.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., 26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es
Busto
Jesús H
JH
Cativiela
Carlos
C
Corzana
Francisco
F
Peregrina
Jesús M
JM
Zurbano
María M
MM
D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C450002:7-tert-butoxycarbonylamino-2-ketocarbacepham; D015780:Carbapenems; D002511:Cephalosporins