Microwave-Assisted Carbonyl–Carbonyl Coupling Route for the Preparation of a Useful Intermediate in the Synthesis of Carbapenems

REFERENCES

• Afonso , A. ; Hon , F. ; Weinstein , J. ; Ganguly , A. K. New synthesis of penems, the oxalimide cyclization reaction . J. Am. Chem. Soc. 1982 , 104 , 6138 – 6139 .
   Google Scholar
• Battistini , C. ; Scarafile , C. ; Foglio , M. ; Franceschi , G. A new route to penems and carbapenems . Tetrahedron Lett. 1984 , 2395 – 2398 .
   Google Scholar
• Yoshida , A. ; Hayashi , T. ; Takeda , N. ; Oida , S. ; Ohki , E. New synthesis of penems via reductive cyclization reaction of oxalimides with trialkyl phosphite . Chem. Phar. Bull. 1983 , 31 , 768 – 771 .
   Google Scholar
• Mori , M. ; Oida , S. A short-step synthesis of orally active carbapenem antibiotic CS-834 . Chem. Pharm. Bull. 2000 , 48 , 126 – 130 .
   Google Scholar
• Bitha , P. ; Lin , Y.-I. Efficient synthesis of oral THF 1β-methylcarbapenem (OCA-983) via the wittig process . Synth. Commun. 2001 , 31 , 587 – 594 .
   Web of Science ®Google Scholar
• Sunagawa , M. ; Matasumura , H. ; Inoue , T. ; Fukasawa , M. ; Kato , M. A novel carbapenem antibiotic, Sm-7338 structure-activity-relationships . J. Antibiotics 1990 , 43 , 519 – 532 .
   PubMed Web of Science ®Google Scholar
• Tamburini , B. ; Perboni , A. ; Rossi , T. ; Donati , D. ; Gaviraghi , G. ; Tarzia , G. Recent Advances in the Chemistry of Anti-infective Agents ; RSC : Cambridge , 1992 .
   Google Scholar
• Panunzio , M. ; Camerini , R. ; Pachera , R. ; Donati , D. ; Marchioro , C. ; Perboni , A. Highly stereocontrolled synthesis of enantiomeric 4-methoxy trinems via resolution of scalemic enol phosphates. Tetrahedron: Asymmetry 1996, 7, 2929–2938.
   Google Scholar
• Panunzio , M. ; Campana , E. ; Martelli , G. ; Vicennati , P. ; Tamanini , E. Microwave in organic synthesis: Myth or reality? . Mat. Res. Innov. 2004 , 8 , 27 – 32 .
   Web of Science ®Google Scholar
• Leanza , W. J. ; Windonger , K. J. ; Miller , T. M. ; Christensen , B. G. N-Acetimidoyl- and N-formimidoylthienamycin derivatives: Antipseudomonal β-lactam antibiotics . J. Med. Chem. 1979 , 22 , 1435 – 1436 .
   PubMed Web of Science ®Google Scholar
• Loupy , A. Microwaves in Organic Synthesis ; Wiley-VCH : Weinheim , 2002 .
   Google Scholar
• Kappe , C. O. The use of microwave irradiation in organic synthesis: From laboratory curiosity to standard practice in twenty years . Chimia 2006 , 60 , 308 – 312 .
   Google Scholar
• Yoshida , A. ; Tajima , Y. ; Takeda , N. ; Oida , S. An efficient carbapenem synthesis via an intramolecular Wittig reaction of new trialkoxyphosphorane-thiolesters . Tetrahedron Lett. 1984 , 25 , 2793 – 2796 .
   Google Scholar
• Perrone , E. ; Alpegiani , M. ; Bedeschi , A. ; Giudici , F. ; Franceschi , G. The carbonyl–carbonyl coupling route to penems: A stepwise analysis . Tetrahedron Lett. 1984 , 25 , 2399 – 2402 .
   Google Scholar