A facile synthesis of (-)-4-phenylsulfonyl-2-azetidinone

Bulletin of the Korean Chemical Society

Volumn 22, Issue 9, 2001, Pages 939-940

  Lee, Kee In ^a   Yoon, Taek Hyun ^a,b   Shim, Young Key ^a   Kim, Wan Joo ^a,c  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Choongwae Pharma Co   (South Korea)

^c Suwon University   (South Korea)

Author keywords

Azetidinone; Cycloaddition; Epoxide ring opening; Sharpless epoxidation

Indexed keywords

4 PHENYLSULFONYL 2 AZETIDINONE; AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; CARBAPENEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0035540390     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. (a) Albers-Schönberg, G.; Arison, B. H.; Hensens, O. D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E. A.; Rhodes, R. E.; Kagan, J. S.; Kagan, F. M.; Ratcliffe, R. W.; Walton, E.; Ruswinkle, L. J.; Morin, R. B.; Christensen, B. J. J. Am. Chem. Soc. 1978, 100, 6491.
2. (b) Kagan, J. S.; Kagan, F. M.; Goegelman, R.; Currie, S. A.; Jackson, M.; Stapley, E. O.; Miller, T. W.; Miller, A. K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H. B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
3. Aznar, J.; García-Iglesias, M. C.; Perea, E. J. J. Antimicrob. Chemother. 1984, 13, 129.
4. Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M.; Kato, M. J. Antibiot. 1990, 43, 519.
5. Ternansky, R. J.; Morin, J. M., Jr. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 257-293.
6. Paloma, C.; Perrone, E.; Franceschi, G. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukas, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; pp 568-573, pp 617-618.
7. Moreno-Manas, M.; Trius, A. Tetrahedron 1981, 37, 3009.
8. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
9. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287.
10. Kang, S.-K.; Park, Y.-W.; Kim, S.-G.; Jeon, J.-H. J. Chem. Soc., Chem. Commun. 1992, 405 and cited references.
11. (a) Takano, S.; Sugihara, Y.; Ogasawara, K. Synlett 1992, 668.
12. (b) Takano, S.; Sugihara, Y.; Ogasawara, K. Tetrahedron Lett. 1993, 34, 845.
13. Ohasi, T.; Kan, K.; Sada, I.; Miyama, A.; Watanabe, K. Eur. Pat. Appl. 167155, 1986; Chem. Abstr. 1986, 105, 60469f.
14. Nakatsuka, T.; Iwata, H.; Tanaka, R.; Imajo, S.; Ishiguro, M. J. Chem. Soc., Chem. Commun. 1991, 662.
15. Shibasaki, M.; Nishida, A.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1982, 1324.