Practical synthesis and applications of benzoboroxoles

Tetrahedron

Volumn 63, Issue 38, 2007, Pages 9401-9405

  Gunasekera, Dinara S ^a   Gerold, Dennis J ^a   Aalderks, Nathan S ^a   Chandra, J Subash ^a   Maanu, Christiana A ^a   Kiprof, Paul ^a   Zhdankin, Viktor V ^a   Reddy, M Venkat Ram ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

Benzoboroxoles; Boronate esters; Boronic acids; C C bond formation; Onychomycosis; Suzuki Miyaura cross coupling

Indexed keywords

ALCOHOL DERIVATIVE; AN 2690; ANTIFUNGAL AGENT; BORONIC ACID DERIVATIVE; LITHIUM DERIVATIVE; PALLADIUM; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CROSS COUPLING REACTION; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 34547577782     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.099     Document Type: Article

References (38)

1. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
2. Suzuki A. J. Organomet. Chem. 576 (1999) 147
3. Sato, S.; Nakamura, T.; Nara, F.; Komesu, K. Jpn. Kokai Tokkyo Koho, JP2005022986, 2005;
4. Falck J.R., Bondlela M., Venkataraman S.K., and Srinivas D. J. Org. Chem. 66 (2001) 7148
5. Gallant M., Belley M., Carriere M.C., Chateauneuf A., Denis D., Lachance N., Lamontagne S., Metters K.M., Sawyer N., Slipetz D., Truchon J.F., and Labelle M. Bioorg. Med. Chem. Lett. 13 (2003) 3813
6. Yamamoto Y., Ishii J., Nishiyama H., and Itoh K. J. Am. Chem. Soc. 127 (2005) 9625
7. Benkovic S.J., Baker S.J., Alley M.R.K., Woo Y.H., Zhang Y.K., Akama T., Mao, Baboval J., Rajagopalan P.T.R., Wall M., Kahng L.S., Tavassoli A., and Shapiro L. J. Med. Chem. 48 (2005) 7468
8. Baker S.J., Zhang Y.K., Akama T., Lau A., Zhou H., Hernandez V., Mao W., Alley M.R.K., Sanders V., and Plattner J.J. J. Med. Chem. 49 (2006) 4447
9. Oshima K., and Aoyama Y. J. Am. Chem. Soc. 121 (1999) 2315
10. Dowlut M., and Hall D.G. J. Am. Chem. Soc. 128 (2006) 4226
11. Nicolaou K.C., Natarajan S., Li H., Jain N.F., Hughes R., Solomon M.E., Ramanjulu J.M., Boody C.N.C., and Takayanagi M. Angew. Chem., Int. Ed. 37 (1998) 2708
12. Nicolaou K.C., Li H., Boody C.N.C., Ramanjulu J.M., Yue T.Y., Natarajan S., Chu X.J., Brase S., and Rubsam F. Chem.-Eur. J. 5 (1999) 2584
13. Tan Y.L., White A.J.P., Widdowson D.A., Wilhelm R., and Williams D.J. J. Chem. Soc., Perkin Trans. 1 (2001) 3269
14. Alexander C., Smith C.R., Whitcombe M.J., and Vulfson E.N. J. Am. Chem. Soc. 121 (1999) 6640
15. Russell, A. P.; Zepp, C. W. U.S. Patent, US5512246, 1996.
16. Lowe, C. R.; Sartain, F. K.; Yang, X. P.C.T. Int. Appl., WO2006079843, 2006.
17. Austin, P. W.; Kneale, C. J.; Crowley, P. J.; Clough, J. M. P.C.T. Int. Appl., WO9533754, 1995.
18. Torssell K. Ark. Kemi. 10 (1957) 507
19. Snyder H.R., Reedy A.J., and Lennarz W.J. J. Am. Chem. Soc. 80 (1958) 835
20. Lennarz W.J., and Snyder H.R. J. Am. Chem. Soc. 82 (1960) 2172
21. Dewar M.J.S., and Dietz R. Tetrahedron Lett. 14 (1959) 21
22. Beermann C., and Clauss K. Angew. Chem. 71 (1959) 627
23. Letsinger R.L., Feare T.E., Savereide T.J., and Nazy J.R. J. Org. Chem. 26 (1961) 1271
24. Dale W.J., and Rush J.R. J. Org. Chem. 27 (1962) 2598
25. Haynes R.R., and Snyder H.R. J. Org. Chem. 29 (1964) 3229
26. Koester R., and Rotermund G.W. Tetrahedron Lett. 25-26 (1964) 1667
27. Dewar M.J.S., and Jones R. J. Am. Chem. Soc. 89 (1967) 2408
28. Cummings W.M., Cox C.H., and Snyder H.R. J. Org. Chem. 34 (1969) 1669
29. Brown H.C., and Cole T.E. Organometallics 2 (1983) 1316
30. Brown A.G., Crimmin M.J., and Edwards P.D. J. Chem. Soc., Perkin Trans. 1 (1992) 123
31. Arcus V.L., Main L., and Nicholson B.K. J. Organomet. Chem. 420 (1993) 139
32. Sporzynski A., Lewandowski M., Rogowska P., and Cyranski M.K. Appl. Organomet. Chem. 19 (2005) 1202
33. Reddy V.J., Chandra J.S., and Reddy M.V.R. Org. Biomol. Chem. 5 (2007) 889
34. Zhdankin V.V., Persichini P.J., Zhang L., Fix S., and Kiprof P. Tetrahedron Lett. 40 (1999) 6705
35. Brown H.C., and Jadhav P.K. J. Org. Chem. 49 (1984) 4089
36. Ramachandran P.V., Chandra J.S., and Reddy M.V.R. J. Org. Chem. 67 (2002) 7547
37. Ramachandran P.V., Prabhudas B., Chandra J.S., and Reddy M.V.R. J. Org. Chem. 69 (2004) 6294
38. Ramachandran P.V., Chandra J.S., Prabhudas B., Pratihar D., and Reddy M.V.R. Org. Biomol. Chem. 3 (2005) 3812