Total syntheses of the telomerase inhibitors dictyodendrin B, C, and E

Journal of the American Chemical Society

Volumn 128, Issue 24, 2006, Pages 8087-8094

  Fürstner, Alois ^a   Domostoj, Mathias M ^a   Scheiper, Bodo ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORATE MINERALS; CATALYSTS; ENZYME INHIBITION; OXIDATION; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING CHEMISTRY; CYCLOADDITION; REDUCTIVE CLEAVAGE; TELOMERASE INHIBITORS;

ENZYMES;

4 METHOXYBENZYLMAGNESIUM CHLORIDE; ALKALOID; AMIDE; BENZENE DERIVATIVE; BENZOQUINONE; BORIC ACID; BORONIC ACID DERIVATIVE; BROMIDE; CARBAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DICTYODENDRIN B; DICTYODENDRIN C; DICTYODENDRIN E; ESTER; MAGNESIUM CHLORIDE; OXOAMIDE; PALLADIUM; PEROXOIMIDIC ACID; PYRROLE DERIVATIVE; PYRROLO[2,3 C]CARBAZOLE; TELOMERASE INHIBITOR; TIN DERIVATIVE; TITANIUM; TRICHLOROETHYL SULFATE ESTER; UNCLASSIFIED DRUG; ZINC;

AROMATIZATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; COUPLING REACTION; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; ELECTROAROMATIZATION; ELECTROCHEMISTRY; ELECTROCYCLIZATION; METAL HALOGEN EXCHANGE; OXIDATION; PHOTOCHEMISTRY; REACTION ANALYSIS; REDUCTION; REDUCTIVE CLEAVAGE; SUZUKI REACTION; SYNTHESIS;

AMIDES; BENZOQUINONES; CARBAZOLES; CATALYSIS; CROSS-LINKING REAGENTS; CYCLIZATION; ENZYME INHIBITORS; HALOGENS; INDOLE ALKALOIDS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PALLADIUM; PHOTOCHEMISTRY; PYRROLES; STEREOISOMERISM; SULFURIC ACID ESTERS; TELOMERASE; TITANIUM; ZINC;

EID: 33745411732     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0617800     Document Type: Article

References (103)

1. (a) Telomeres; Blackburn, E. H., Greider, C. W., Eds.; Cold Spring Harbor Lab: Plainview, NY, 1995.
2. (b) Cech, T. R. Angew. Chem., Int. Ed. 2000. 39, 34.
3. (a) Greider, C. W.; Blackburn, E. H. Cell 1985, 43, 405.
4. (b) Morin, G. B. Cell 1989, 59, 521.
5. For a very recent first structural investigation on telomerase, see: Jacobs, S. A.; Podell, E. R.; Cech, T. R. Nat. Struct Mol. Biol. 2006, 13, 218.
6. Reviews: (a) Neidle, S.; Parkinson, G. Nat. Rev. Drug Discovery 2002, 1, 383.
7. (b) Neidle, S.; Thurston, D. E. Nat. Rev. Cancer 2005, 5, 285.
8. (c) Kelland, L. R. Eur. J. Cancer 2005, 41, 971.
9. (d) Beltz, L. A.; Manfredi, K. P. Med. Chem. Rev.-Online 2005, 2, 325.
10. See the following tor leading references and literature cited therein: (a) Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L. C.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Science 1994, 266, 2011.
11. (b) Herbert, B.-S.; Pitts, A. E.; Baker, S. I.; Hamilton, S. E.; Wright, W. E.; Shay, J. W.; Corey, D. R. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14276.
12. (c) Keppler, B. R.; Jarstfer, M. B. Biochemistry 2004, 43, 334.
13. (d) Hahn, W. C.; Stewart, S. A.; Brooks, M. W.; York, S. G.; Eaton, E.; Kurachi, A.; Beijersbergen, R. J.; Knoll, J. H. M.; Meyerson, M.; Weinberg, R. A. Nat. Med. 1999, 5, 1164.
14. For leading references on synthetic telomerase inhibitors, see the following references and literature cited therein: (a) Moore, M. J. B.; Schultes, C. M.; Cuesta, J.; Cuenca, F.; Gunaratnam, M.; Tanious, F. A.; Wilson, W. D.; Neidle, S. J. Med. Chem. 2006, 49, 582.
15. (b) Pascolo, E.; Wenz, C.; Lingner, J.; Hauel, N.; Priepke, H.; Kauffmann, I.; Garin-Chesa, P.; Rettig, W. J.; Damm, K.; Schnapp, A. J. Biol. Chem. 2002, 277, 15566.
16. For selected studies of natural products with telomerase inhibitory properties, see: (a) Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
17. (b) Lambert, T. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 426.
18. (c) Kim, M.-Y.; Vankayalapati, H.; Shin-ya, K.; Wierzba, K.; Hurley, L. H. J. Am. Chem. Soc. 2002, 124, 2098.
19. (d) Warabi, K.; Hamada, T.; Nakao, Y.; Matsunaga, S.; Hirota, H.; van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2005, 127, 13262.
20. Drills from the Sea; Fusetani, N., Ed.; Karger: Basel, 2000.
21. Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 2003, 68, 2765.
22. Sato, A.; Morishita, T.; Shiraki, T.; Yoshioka, S.; Horikoshi, H.; Kuwano, H.; Hanzawa, H.; Hata, T. J. Org. Chem. 1993, 58, 7632.
23. (a) Bailly, C. Curr. Med. Chem.; Anti-Cancer Agents 2004, 4, 363.
24. (b) Handy, S. T.; Zhang, Y. Org. Prep. Proced. Int. 2005, 17, 411.
25. For selected studies directed to the synthesis of such pyrrole alkaloids, see, e.g.: (a) Hamasaki, A.; Zimpleman, J. M.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2005, 127, 10767.
26. (b) Pla, D.; Marchai, A.; Olsen, C. A.; Albericio, F.; Alvarez, M. J. Org. Chem. 2005, 70, 8231.
27. (c) Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005, 70, 5119.
28. (d) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2362.
29. (e) Iwao, M.; Takeuchi, T.; Fujikawa, N.; Fukuda, T.; Ishibashi, F. Tetrahedron Lett. 2003, 44, 4443.
30. (f) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439.
31. (g) Gupton, J. T.; Clough, S. C.; Miller, R. B.; Lukens, J. R.; Henry, C. A.; Kanters, R. P. F.; Sikorski, J. A. Tetrahedron 2003, 59, 207.
32. (h) Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
33. (i) Boger, D. L.; Soenen, D. R.; Boyce, C. W.; Hedrick, M. P.; Jin, Q. J. Org. Chem. 2000, 65, 2479.
34. (j) Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
35. (k) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
36. (l) Peschko, C.; Winklhofer, C.; Steglich, W. Chem.-Eur. J. 2000, 6, 1147.
37. (m) Peschko, C.; Steglich, W. Tetrahedron Lett. 2000, 41, 9477.
38. (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.
39. (b) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373.
40. (c) Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582.
41. Preliminary communication: Fürstner, A.; Domostoj, M. M.; Scheiper, B. J. Am. Chem. Soc. 2005, 127, 11620.
42. For studies on other bioactive pyrrole alkaloids from our group, see: (a) Fürstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777.
43. (b) Fürstner, A.; Reinecke, K.; Prinz, H.; Waldmann, H. ChemBioChem 2004, 5, 1575.
44. (c) Fürstner, A.; Grabowski, E. J. ChemBioChem 2001, 2, 706.
45. (d) Fürstner, A.; Grabowski, J.; Lehmann, C. W.; Kataoka, T.; Nagai, K. ChemBioChem 2001, 2, 60.
46. (e) Fürstner, A.; Krause, H. J. Org. Chem. 1999, 64, 8281.
47. (f) Fürstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275.
48. (g) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
49. Butenandt, A.; Hallmann, G.; Beckmann, R. Chem. Ber. 1957, 90, 1120.
50. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Leusen, D. Tetrahedron Lett. 1972, 13, 5337.
51. Prepared in three simple steps from commercial p-hydroxyphenylpyruvic acid; for details, consult the Supporting Information.
52. (a) Fürstner, A.; Hupperts, A.; Ptock, A.; Janssen, E. J. Org. Chem. 1994, 59, 5215.
53. (b) Fürstner, A.; Jumbam, D. N. Tetrahedron 1992, 48, 5991.
54. (a) Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2442.
55. (b) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
56. Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164.
57. (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
58. (b) Fürstner, A.; Hupperts, A.; Seidel, G. Org. Synth. 1999, 76, 142.
59. (c) Fürstner, A.; Seidel, G. Synthesis 1995, 63.
60. (a) Fürstner, A.; Jumbam, D. N. J. Chem. Soc., Chem. Commun. 1993, 211.
61. (b) Fürstner, A.; Ptock, A.; Weintritt, H.; Goddard, R.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 678.
62. (a) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773.
63. (b) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329.
64. (c) Fürstner, A.; Jumbam, D. N.; Seidel, G. Chem. Ber. 1994, 127, 1125.
65. Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985, 26, 2423.
66. Reviews on carbazole synthesis: (a) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
67. (b) Kawasaki, T.; Sakamoto, M. J. Indian Chem. Soc. 1994, 71, 443.
68. (a) Liu, Y.; Lien, I. F.; Ruttgaizer, S.; Dove, P.; Taylor, S. D. Org. Lett. 2004, 6, 209.
69. (b) For a recent application, see: Yamaguchi, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. Tetrahedron Lett. 2006, 47, 3755.
70. Brooks, P. R.; Wirtz, M. C.; Vetelino, M. G.; Rescek, D. M.; Woodworth, G. F.; Morgan, B. P.; Coe, J. W. J. Org. Chem. 1999, 64, 9719.
71. 2/MeCN protocol had to be implemented. This method has the additional advantage that no extractive workup is necessary, thus making the isolation of the very polar final product much more efficient and convenient.
72. For a discussion, see the following for leading references and literature cited therein: (a) Shu, L.; Shi, Y. J. Org. Chem. 2000, 65, 8807.
73. (b) Payne, G. B.; Deming, P. H.; Williams, P. H. J. Org. Chem. 1961, 26, 659.
74. For related oxidations of pyrroles, see: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062.
75. (b) Auerbach, J.; Franck, R. W. J. Chem. Soc. D 1969, 991.
76. For a related maneuver in the total synthesis of a complex pyrrole alkaloid, see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
77. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944.
78. The preparation of compound 23 essentially follows the route described for 18; details will be reported in a forthcoming paper describing various analogues of the naturally occurring dictyodendrins.
79. Carbonium Ions; Olah, G. A., von R. Schleyer, P., Eds.; Wiley: New York, 1970; Vol. 2.
80. Although base-induced "halogen dance" processes are well-known in (hetero)arene chemistry (cf.: Duan, X.-F.; Zhang, Z.-B. Heterocycles 2005, 65, 2005 and literature cited therein)
81. 3 was used, it is assumed that traces of acid are generated upon reaction with the solvent that might catalyze the observed halide shift, cf. ref 36.
82. MS analysis shows that traces of a dibrominated compound and a compound containing one bromine and one chlorine atom are formed as byproducts during this halide walk. Although incorporation of a chloride derived from the solvent might give some mechanistic hints, the exact constitution of these minor products has not been investigated any further.
83. The sequential use of MeLi and n-BuLi for a deprotonation/metal-halogen exchange tandem has precedence in the literature; for an early example and an instructive discussion, see: Kelly. T. R.: Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072.
84. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
85. A related process is reported in: Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfarth, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
86. Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393.
87. Flaherty, A.; Trunkfield, A.; Barton, W. Org. Lett. 2005, 7, 4975.
88. (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165.
89. (b) Fürstner, A.; Leitner, A. Synlett 2001, 290.
90. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107.
91. (d) The method was also independently reported by: Soderquist, J. A.; Mato.s, K.; Rane, A.; Ramos, J. Tetrahedron Lett. 1995, 36, 2401.
92. This method had previously allowed for very efficient allylations of aryl halides; cf.: Fürstner, A.; Seidel, G. Synlett 1998, 161.
93. For general reviews on the Suzuki reaction, see, e.g.: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
94. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
95. (a) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
96. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
97. 2 previously recommended for Suzuki reactions according to the "9-MeO-9-BBN" protocol failed to afford the cross-coupling product. This is tentatively ascribed to the electronrich nature of substrate 27, which renders the use of the more electron-donating and sterically demanding S-PHOS ligand imperative for successful oxidative insertion of the Pd(O) template.
98. Control experiments showed the MeOH addition to be complete after ca. 1 week at ambient temperature in the absence of external catalysts.
99. This notion is supported by several recent applications of the 9-MeO-9-BBN variant of the Suzuki reaction which were difficult or impossible to achieve under standard conditions; cf.: (a) Fürstner, O.; Turet, L. Angew. Chem., Int. Ed. 2005, 44, 3462.
100. (b) Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
101. (c) Yuan, Y.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 14720.
102. (d) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
103. (e) Mickel, S. J. et al., Org. Process Res. Dev. 2004, 8, 113-121.