Enantiomerically pure polyheterocyclic spiro-beta-lactams from trans-4-hydroxy-L-proline.
The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-l-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C=C double bond was submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.
Cremonesi
Giuseppe
G
DISMAB-Sezione di Chimica Organica A. Marchesini, Università degli Studi di Milano, V. Venezian 21, I-20133 Milano, Italy.
Dalla Croce
Piero
P
Fontana
Francesco
F
La Rosa
Concetta
C
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D006571:Heterocyclic Compounds; D011758:Pyrroles; D013141:Spiro Compounds; D047090:beta-Lactams; D011392:Proline