Aryllead(IV) reagents in synthesis: Formation of the C11 quaternary center of N-Methylwelwitindolinone C isothiocyanate

Organic Letters

Volumn 3, Issue 19, 2001, Pages 3001-3004

  Deng, Hongbo ^a   Konopelski, Joseph P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; GLYCOPROTEIN P; LEAD; N METHYLWELWITINDOLINONE C ISOTHIOCYANATE; N-METHYLWELWITINDOLINONE C ISOTHIOCYANATE;

ARTICLE; CHEMISTRY; CYANOBACTERIUM; DRUG ANTAGONISM; MULTIDRUG RESISTANCE; SYNTHESIS;

ALKALOIDS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; CYANOBACTERIA; DRUG RESISTANCE, MULTIPLE; LEAD; P-GLYCOPROTEIN;

EID: 0035922365     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016379r     Document Type: Article

References (33)

1. Stratmann, K.; Moore, R. E.; Bonjouklian, R., Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc. 1994, 116, 9935.
2. (a) Wood, J. L.; Holubec, A. A., Stoltz, B. M.; Weiss, M. M.; Dixon, J. A.; Doan, B. D.; Shamji, M. F.; Chen, J. M.; Heffron, T. P. J. Am. Chem. Soc. 1999, 121, 6326. (b) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371.
3. (a) Wood, J. L.; Holubec, A. A., Stoltz, B. M.; Weiss, M. M.; Dixon, J. A.; Doan, B. D.; Shamji, M. F.; Chen, J. M.; Heffron, T. P. J. Am. Chem. Soc. 1999, 121, 6326. (b) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371.
4. Taken in part from: Deng, H.; Konopelski, J. P. 220th National Meeting of the American Chemical Society, Washington, DC, August 20-24, 2000, paper ORGN 11.
5. Konopelski, J. P.; Deng, H.; Schieman, K.; Keane, J. M.; Olmstead, M. M. Synlett 1998, 1105.
6. Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353.
7. Phillips, R. S.; Cohen, L. A. J. Am. Chem. Soc. 1986, 108, 2023.
8. Finet, J. P. Ligand Coupling Reactions with Heteroatomic Compounds; Pergamon Press: Oxford, 1998.
9. Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683.
10. Konopelski, J. P.; Hottenroth, J. M.; Monzó-Oltra, H.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609.
11. Donnelly, D. M. X.; Finet, J. P.; Kiety, J. M. Tetrahedron Lett. 1991, 32, 3835.
12. Soriano, D. S. J. Chem. Educ. 1993, 70, 332.
13. Andreani, A.; Bonazzi, D.; Rambaldi, M.; Guarnieri, A.; Andreani, F.; Strocchi, P.; Montanaro, N. J. Med. Chem. 1977, 20, 1344.
14. Showalter, H. D. H.; Sercel, A. D.; Leja, B. M.; Wolfangel, C. D.; Ambrose, L. A.; Wlliott, W. L.; Fry, D. W.; Kraker, A. J.; Howard, C. T.; Lu, G. H.; Moore, C. W.; Nelson, J. M.; Roberts, B. J.; Vincent, P. W.; Denny, W. A.; Thompson, A. M. J. Med. Chem. 1997, 40, 413.
15. Coppola, G. M.; Hardtmann, G. E. J. Heterocycl. Chem. 1977, 14, 1117.
16. Kozyrod, R. P.; Pinhey, J. T. Org. Synth. 1984, 62, 24.
17. Hollins, R. A.; Colnago, L. A.; Salin, V. M.; Seidl, M. C. J. Heterocycl. Chem. 1979, 16, 993.
18. Somei, M.; Yamada, F.; Kunimoto, M.; Kaneko, C. Heterocycles 1984, 22, 797.
19. Tueting, D. R.; Echavarren, A. M.; Stille, J. K. Tetrahedron 1989, 45, 979.
20. Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1147.
21. Kozyrod, R. P.; Pinhey, J. T. Tetrahedron Lett. 1983, 24, 1301.
22. In separate experiments, 13-15 were prepared and also failed to afford tin-lead exchange products. It is believed that steric and/or electronic factors arising from the close proximity of the C4 and C3 substituents on the indole nucleus are involved
23. (a) Moyer, M. P.; Shiruba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51, 5106. (b) Doll, M. K-H. J. Org. Chem. 1999, 64, 1372.
24. (a) Moyer, M. P.; Shiruba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51, 5106. (b) Doll, M. K-H. J. Org. Chem. 1999, 64, 1372.
25. Grehn, L.; Ragnarsson, U. Angew. Chem., Int. Ed. Engl. 1984, 23, 296.
26. Elliott, G. I.; Konopelski, J. P.; Olmstead, M. M. Org Lett. 1999, 1, 1867.
27. Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141.
28. (a) Saladino, R.; Mezzetti, M.; Mincione, E.; Torrini, I.; Paradisi, A. P.; Mastropietro, G. J. Org. Chem. 1999, 64, 8468. (b) Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867. Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227.
29. (a) Saladino, R.; Mezzetti, M.; Mincione, E.; Torrini, I.; Paradisi, A. P.; Mastropietro, G. J. Org. Chem. 1999, 64, 8468. (b) Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867. Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227.
30. (a) Saladino, R.; Mezzetti, M.; Mincione, E.; Torrini, I.; Paradisi, A. P.; Mastropietro, G. J. Org. Chem. 1999, 64, 8468. (b) Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867. Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227.
31. Rajeswaren, W. G.; Labroo, R. B.; Cohen, L. C. J. Org. Chem. 1999, 64, 1369. (b) Lawson, W. B.; Witkop, B. J. Org. Chem. 1961, 26, 263. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 1206.
32. Rajeswaren, W. G.; Labroo, R. B.; Cohen, L. C. J. Org. Chem. 1999, 64, 1369. (b) Lawson, W. B.; Witkop, B. J. Org. Chem. 1961, 26, 263. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 1206.
33. Rajeswaren, W. G.; Labroo, R. B.; Cohen, L. C. J. Org. Chem. 1999, 64, 1369. (b) Lawson, W. B.; Witkop, B. J. Org. Chem. 1961, 26, 263. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 1206.