Diastereoselective synthesis of a key intermediate for the preparation of tricyclic β-lactam antibiotics

✍ Scribed by Takaji Matsumoto; Toshiyuki Murayama; Shigeru Mitsuhashi; Takashi Miura

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 236 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00929-6

✦ Synopsis

Asymmetric synthesis of (S)-5 has been accomplished with an excellent enantiomeric excess by hydrogenation of raeemie 5 using ruthenium-BINAP-diamine-KOH system, followed by oxidation. Magnesium enolate of (2S)-2-methoxycyclohexanone [(S)-5] reacts with the 4-aeetoxyazetidinone 4 to give the key intermediate 3 with high yield and diastereoseleetivity for the synthesis of sanfetrinem 1.