Stereoselective synthesis of fluorine-containing analogues of anti-bacterial sanfetrinem and LK-157

Tetrahedron

Volumn 66, Issue 23, 2010, Pages 4144-4149

  Mohar, Barbara ^a   Stephan, Michel ^a   Urleb, Uroš ^b  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b Lek dd   (Slovenia)

Author keywords

Lactam; Asymmetric transfer hydrogenation; Ruthenium; Total synthesis

Indexed keywords

ANTIINFECTIVE AGENT; AZETIDINONE DERIVATIVE; BICARBONATE; CYCLOHEXENE DERIVATIVE; ETHYLIDENE 4 METHOXYTRINEM; FLUORINE; LITHIUM; LK 157; RUTHENIUM COMPLEX; SANFETRINEM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

BACTERIA (MICROORGANISMS);

EID: 77953094163     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.104     Document Type: Article

References (53)

1. Bentley P.H., and Ponsford R. Recent Advances in the Chemistry of Anti-infective Agents (1992), The Royal Society of Chemistry, Cambridge
2. Massova I., and Mobashery S. Acc. Chem. Res. 30 (1997) 162-168
3. Bonfiglio G., Russo G., and Nicoletti G. Expert Opin. Invest. Drugs 11 (2002) 529-544
4. Deshmukh A.R.A.S., Bhawal B.M., Krishnaswamy D., Govande V.V., Shinkre B.A., and Jayanthi A. Curr. Med. Chem. 11 (2004) 1889-1920
5. Yoneyama H., and Katsumata R. Biosci. Biotechnol. Biochem. 70 (2006) 1060-1075
6. Andreotti D., Rossi T., Gaviraghi G., Donati D., Marchioro C., Di Modugno E., and Perboni A. Bioorg. Med. Chem. Lett. 6 (1996) 491-496
7. Perboni, A.; Rossi, T.; Gaviraghi, G.; Ursini, A.; Tarzia, G. WO9203437, 1992.
8. Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C. EP0416953, 1991.
9. Annunziata R., Benaglia M., Cinquini M., Cozzi F., Poletti L., Raimondi L., and Perboni A. Eur. J. Org. Chem. 11 (1999) 3067-3072
10. Iso Y., and Nishitani Y. Heterocycles 48 (1998) 2287-2308
11. Biondi S., Piga E., Rossi T., and Vigelli G. Bioorg. Med. Chem. Lett. 7 (1997) 2061-2066
12. Hanessian S., Griffin A.M., and Rozema M.J. Bioorg. Med. Chem. Lett. 7 (1997) 1857-1862
13. Rossi T. Soc. Chim. Ital. 1 (1997) 161-186
14. Jackson P.M., Roberts S.M., Davalli S., Donati D., Marchioro C., Perboni A., Proviera S., and Rossi D. J. Chem. Soc., Perkin Trans. 1 (1996) 2029-2039
15. Hanessian R., and Rozema M.J. J. Am. Chem. Soc. 118 (1996) 9884-9891
16. Gaviraghi G. Eur. J. Med. Chem. 30 (1995) 467-478
17. Vilar M., Galleni M., Šolmajer T., Turk B., Frere J.M., and Matagne A. Antimicrob. Agents Chemother. 45 (2001) 2215-2223
18. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-organic Compounds (1999), Wiley, Chichester, UK
19. Mikami K. In: Ramachandran P.V. (Ed). Asymmetric Fluoroorganic Chemistry: Synthesis, Application and Future Directions (2000), American Chemical Society, Washington, DC 255-269
20. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1-16
21. Plantan I., Selič L., Mesar T., Štefanič Anderluh P., Oblak M., Prezelj A., Hesse L., Andrejašič M., Vilar M., Turk D., Kocijan A., Prevec T., Vilfan G., Kocjan D., Čopar A., Urleb U., and Šolmajer T. J. Med. Chem. 50 (2007) 4113-4121
22. Rossi T., Marchioro C., Paio A., Thomas R.J., and Zarantonello P. J. Org. Chem. 62 (1997) 1653-1661
23. Antolini L., Forni A., Davoli P., Moretti I., and Prati F. Tetrahedron: Asymmetry 9 (1998) 285-292
24. Sayo, N.; Saito, T.; Okeda, Y.; Nagashima, H.; Kumobayashi, H. EP0369691, 1990.
25. Noyori R., Ikeda T., Ohkuma T., Widhalm M., Kitamura M., Takaya H., Akutagawa S., Sayo N., Saito T., Taketomi T., and Kumobayashi H. J. Am. Chem. Soc. 111 (1989) 9134-9135
26. 2DPEN]-catalyzed asymmetric transfer hydrogenation of a β-keto-α-amino ester via DKR, see:. Mohar B., Valleix A., Desmurs J.-R., Felemez M., Wagner A., and Mioskowski C. Chem. Commun. (2001) 2572-2573
27. Šterk D., Stephan M.S., and Mohar B. Tetrahedron: Asymmetry 13 (2002) 2605-2608
28. Šterk D., Stephan M.S., and Mohar B. Org. Lett. 8 (2006) 5935-5938
29. The syn/anti configurations for 4 were assigned based on the separate transformation of the stereoisomers into their corresponding (E)- and (Z)-olefins by stereoselective dehydration under Mitsunobu's conditions. For this, see Supporting data.
30. 4 in MeOH at 0 °C led to syn/anti ratio of 13:87. For this, see Supporting data.
31. 2DPEN] afforded the corresponding syn-β-hydroxy ester with 96% ee and a dr of 83:17. For this, see:
32. Plantan I., Stephan M., Urleb U., and Mohar B. Tetrahedron Lett. 50 (2009) 2676-2677
33. Plantan, I.; Preželj, A.; Urleb, U.; Mohar, B.; Stephan, M. EP158454, 2008.
34. Kobayashi S., Iimori T., Izawa T., and Ohno M. J. Am. Chem. Soc. 103 (1981) 2406-2408
35. Greene T.W., and Wuts G.M. Protective Groups in Organic Synthesis (1999), John Wiley & Sons, New York, NY
36. We also failed to acetoxylate the new N-TBDMS-protected azetidinone 7 following standard literature procedures. For adopted conditions, see:
37. Murahashi S.-I., Naota T., Kuwabara T., Saito T., Kumobayashi H., and Akutagawa S. J. Am. Chem. Soc. 112 (1990) 7820-7822
38. Murahashi S.-I., Saito T., Naota T., Kumobayashi H., and Akutagawa S. Tetrahedron Lett. 32 (1991) 5991-5994
39. 3-catalyzed oxidation gave a complex mixture. For this, see:. Murahashi S.-I., Saito T., Naota T., Kumobayashi H., and Akutagawa S. Tetrahedron Lett. 32 (1991) 2145-2148
40. CCDC 751242 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre (12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033, or deposit@ccdc.cam.ac.uk).
41. The displacement of the acetoxy group from (1′R,3R,4R)-4-acetoxy-3-[1′-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone using O-TMS-enol ether or metal (Mg, Zn, Zr, Sn) enolates of (S)-2-methoxycyclohexanone has been shown to be a reasonably stereoselective C-C coupling reaction. For examples of this, see:
42. Ref. 7;
43. Matsumoto T., Murayama T., Mitsuhashi S., and Miura T. Tetrahedron Lett. 40 (1999) 5043-5046
44. Ghiron C., Piga E., Rossi T., Tamburini B., and Thomas R.J. Tetrahedron Lett. 37 (1996) 3891-3894
45. Kennedy G., Rossi T., and Tamburini B. Tetrahedron Lett. 37 (1996) 7441-7444
46. Giacobbe S.A., and Rossi T. Tetrahedron: Asymmetry 7 (1996) 3079-3082
47. Ernest I., Gosteli J., and Woodward R.B. J. Am. Chem. Soc. 101 (1979) 6301-6305
48. Perrone E., Alpegiani M., Bedeschi A., Giudici F., and Franceschi G. Tetrahedron Lett. 25 (1984) 2399-2402
49. Yoshida A., Tajima Y., Takeda N., and Oida S. Tetrahedron Lett. 25 (1984) 2793-2796
50. Jeffrey P.D., and McCombie S.W. J. Org. Chem. 47 (1982) 587-590
51. Böhme, H.; Eiden, F. DE1025883, 1958.
52. Böhme H., Broese R., and Eiden F. Chem. Ber. 92 (1959) 1599-1607
53. Phillips B., Starcher P.S., and Ash B.D. J. Org. Chem. 23 (1959) 1823-1826