title: Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by (2 + 2) cycloaddition of diketene and Schiff bases.
abstract: It was found that (2 + 2) cycloaddition reaction of diketene with Schiff bases was effectively promoted by imidazole as a catalyst to afford 3-acetyl-2-azetidinone derivatives 4. As an application of this new method, a practical asymmetric synthesis of 4 and its conversion into (3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-[(R)-1-hydroxyethyl]-2- azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, were accomplished.
authors.affiliation: Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd., Osaka, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Sasaki
authors.forename: K
authors.initials: K
authors.lastname: Goda
authors.forename: M
authors.initials: M
authors.lastname: Enomoto
authors.forename: M
authors.initials: M
authors.lastname: Sunagawa
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001384:Azetidines / Q000138:chemical synthesis*; D015780:Carbapenems / Q000138:chemical synthesis*; D012545:Schiff Bases / Q000138:chemical synthesis*
chemical_list: D000900:Anti-Bacterial Agents; D001384:Azetidines; D015780:Carbapenems; D012545:Schiff Bases