Phorboxazole synthetic studies: Design, synthesis and biological evaluation of phorboxazole A and hemi-phorboxazole A related analogues

Tetrahedron

Volumn 67, Issue 27-28, 2011, Pages 5069-5078

  Smith III, Amos B ^a   Hogan, Anne Marie L ^a   Liu, Zhuqing ^a   Razler, Thomas M ^a   Meis, Regina M ^a   Morinaka, Brandon I ^b   Molinski, Tadeusz F ^b,c  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; FURAN; HEMI PHORBOXAZOLE A; OXAZOLE; PHENYL GROUP; PHORBOXAZOLE A; PHORBOXAZOLE ANALOG; TETRAHYDROPYRAN DERIVATIVE; THIAZOLE; THIOPHENE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANDIDA ALBICANS; CYTOTOXICITY; DRUG CONFORMATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; IC 50; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CANDIDA ALBICANS;

EID: 79958757089     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.043     Document Type: Article

References (50)

1. (a) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126;
2. (b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422;
3. (c) Molinski, T. F. Tetrahedron Lett. 1996, 37, 7879.
4. (a) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc.1998, 120, 5597;
5. (b) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033;
6. (c) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 4834;
7. (d) Gonzalez, M. A.; Pattenden, G. Angew. Chem., Int. Ed. 2003, 42, 1255;
8. (e) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem., Int. Ed. 2003, 42, 1258;
9. (f) Li, D.-R.; Zhang, D.-H.; Sun, C.-Y.; Zhang, J.-W.; Yang, L.; Chen, J.; Liu, B.; Su, C.; Zhou, W.-S.; Lin, G.-Q. Chem. - Eur. J. 2006,12,1185;
10. (g) White, J. D.; Lee, T. H.; Kuntiyong, P. Org. Lett. 2006, 8, 6043;
11. (h) Lucas, B. S.; Gopalsamuthiram, V.; Burke, S. D. Angew. Chem., Int. Ed. 2007, 46, 769 and references therein.
12. For additional publications towards the total synthesis of the phorboxazoles see: (a) Vitale, J. P.; Wolckenhauer, S. A.; Do, N. M.; Rychnovsky, S. D. Org. Lett. 2005, 7, 3255;
13. (b) Yadav, J. S.; Prakash, S. J.; Gangadhar, Y. Tetrahedron: Asymmetry 2005, 16, 2722;
14. (c) Paterson, I.; Steven, A. Org. Biomol. Chem. 2004, 2, 3026;
15. (d) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469;
16. (e) Wolbers, P.; Hoffman, H. M. R. Tetrahedron 1999, 55, 1905 and references therein.
17. Smith, A. B., III; Fox, R. J.; Razler, T. M. Acc. Chem. Res. 2008, 41, 675.
18. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
19. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
20. Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426.
21. (a) Smith, A. B., III; Safonov, I. G. Org. Lett. 2002, 4, 635;
22. (b) Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2002, 124, 11102.
23. Smith, A. B., III; Sfouggatakis, C.; Risatti, C. A.; Sperry, J. B.; Zhu, W.; Doughty, V. A.; Tomioka, T.; Gotchev, D. B.; Bennett, C. S.; Sakamoto, S.; Atasoylu, O.; Shirakami, S.; Bauer, D.; Takeuchi, M.; Koyanagi, J.; Sakamoto, Y. Tetrahedron 2009, 65, 6489.
24. (a) Smith, A. B., III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2005, 127, 6948;
25. (b) Smith, A. B., III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2006, 128, 5292.
26. Smith, A. B., III; Simov, V. Org. Lett. 2006, 8, 3315.
27. Smith, A. B., III; Basu, K.; Bosanac, T. J. Am. Chem. Soc. 2007, 129, 14872.
28. De Lima, C.; Julia, M.; Verpeaux, J.-N. Synlett 1992, 133.
29. (a) Smith, A. B., III; Razler, T. M.; Ciavarri, J. P.; Hirose, T.; Ishikawa, T. Org. Lett. 2005, 7, 4399;
30. (b) Smith, A. B., III; Razler, T. M.; Ciavarri, J. P.; Hirose, T.; Ishikawa, T.; Meis, R. M. J. Org. Chem. 2008, 73, 1192.
31. (a) Smith, A. B., III; Razler, T. M.; Pettit, G. R.; Chapuis, J.-C. Org. Lett. 2005, 7, 4403;
32. (b) Smith, A. B., III; Razler, T. M.; Meis, R. M.; Pettit, G. R. Org. Lett. 2006, 8, 797;
33. (c) Smith, A. B., III; Razler, T. M.; Meis, R. M.; Pettit, G. R. J. Org. Chem. 2008, 73, 1201.
34. Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, F. C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; Lacote, E.; Lippa, B.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648.
35. Smith, A. B., III; Liu, Z.; Hogan, A.-M. L.; Dalisay, D. S.; Molinski, T. F. Org. Lett. 2009, 11, 3766.
36. Dalisay, D. S.; Molinski, T. F. Org. Lett. 2009, 11, 1967.
37. (a) MacMillan, J. B.; Xiong-Zhou, G.; Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2008, 73, 3699;
38. (b) Skepper, C. K.; MacMillan, J. B.; Zhou, G.-X.; Masuno, M. N.; Molinski, T. F. J. Am. Chem. Soc. 2007, 129, 4150;
39. (c) Dalisay, D. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 739.
40. Dalisay, D. S.; Morinaka, B. I.; Skepper, C. K.; Molinski, T. F. J. Am. Chem. Soc. 2009, 131, 7552.
41. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
42. For related transformations see: (a) Duffey, M. O.; LeTiran, A.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 1458;
43. (b) Nicolaou, K. C.; Pratt, B. A.; Arseniyadis, S.; Wartmann, M.; O'Brate, A.; Giannakakou, P. ChemMedChem 2006, 1, 41.
44. Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318.
45. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
46. MTS: 3-4,5-dimethylthiazol-2-yl)-5-3-carboxymethoxyphenyl)-2-4- sulfophenyl)- 2H-tetrazolium inner salt), Promega CellTiter 96® Aqueous cell proliferation assay, Technical Bulletin No. 169.
47. (a) Uckun, F. M.; Forsyth, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1181;
48. (b) Uckun, F. M.; Narla, R. K.; Forsyth, C.; Lee, C.-S.; Ahmed, F.; Cink, R. D. U.S. Patent No. 6,797,721 B2, 2004.
49. Mulder, R. J.; Shafer, C. M.; Dalisay, D. S.; Molinski, T. F. Bioorg. Med. Chem. Lett. 2009, 19, 2928.
50. National Committee for Clinical Laboratory Standards Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, 2nd ed.; Approved standard M27-A2. National Committee for Clinical Laboratory Standards: Wayne, PA, 2002.