Total synthesis of the antimitotic bicyclic peptide celogentin C

Journal of the American Chemical Society

Volumn 132, Issue 3, 2010, Pages 1159-1171

  Ma, Bing ^a   Banerjee, Biplab ^a   Litvinov, Dmitry N ^a   He, Liwen ^a   Castle, Steven L ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-TUMORS; CANCER CELL LINES; CONCENTRATION OF; DEPROTECTION; DIASTEREO-SELECTIVITY; HIGH YIELD; HYDROGEN ATOMS; KNOEVENAGEL CONDENSATION; MACROCYCLES; NATURAL PRODUCTS; OXIDATIVE COUPLINGS; RADICAL CONJUGATE ADDITIONS; REACTION MIXTURE; RING SYNTHESIS; RING SYSTEMS; SIDE-CHAIN; STEP SEQUENCES; SYNTHETIC APPROACH; SYNTHETIC STRATEGIES; TOTAL SYNTHESIS;

ALDEHYDES; CELL CULTURE; ESTERS;

SYNTHESIS (CHEMICAL);

ALDEHYDE; ANTIMITOTIC AGENT; CELOGENTIN C; CYCLOPEPTIDE; HISTIDINE; HYDROGEN; IMIDAZOLE; INDOLE; LEUCINE; MACROCYCLIC COMPOUND; PROLINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CROSS LINKING; DEPROTECTION REACTION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; KNOEVENAGEL CONDENSATION; MACROLACTAMIZATION; OXIDATION; PH; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 76149144042     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909870g     Document Type: Article

References (74)

1. Kobayashi, J.; Suzuki, H.; Shimbo, K.; Takeya, K.; Morita, H. J. Org. Chem. 2001, 66, 6626.
2. (a) Leung, T.-W. C.; Williams, D. H.; Barna, J. C. J.; Foti, S.; Oelrichs, P. B. Tetrahedron 1986, 42, 3333.
3. (b) Kahn, S. D.; Booth, P. M.; Waltho, J. P.; Williams, D. H. J. Org. Chem. 1989, 54, 1901.
4. Suzuki, H.; Morita, H.; Iwasaki, S.; Kobayashi, J. Tetrahedron 2003, 59, 5307.
5. Suzuki, H.; Morita, H.; Shiro, M.; Kobayashi, J. Tetrahedron 2004, 60, 2489.
6. (a) Hase, K.; Kadota, S.; Basnet, P.; Takahashi, T.; Namba, T. Biol. Pharm. Bull. 1996, 19, 567.
7. (b) Hayakawa, Y.; Fujii, H.; Hase, K.; Ohnishi, Y.; Sakukawa, R.; Kadota, S.; Namba, T.; Saiki, I. Biol. Pharm. Bull. 1998, 21, 1154.
8. Morita, H.; Shimbo, K.; Shigemori, H.; Kobayashi, J. Bioorg. Med. Chem. Lett. 2000, 10, 469.
9. Yuen, A. K. L.; Jolliffe, K. A.; Hutton, C. A. Aust. J. Chem. 2006, 59, 819.
10. Grimley, J. S.; Wandless, T. J. Abstracts of Papers, 232nd ACS National Meeting; San Francisco, CA, Sept. 10-14, 2006; ORGN-735.
11. Michaux, J.; Retailleau, P.; Campagne, J.-M. Synlett 2008, 1532.
12. (a) Bentley, D. J.; Slawin, A. M. Z.; Moody, C. J. Org. Lett. 2006, 8, 1975.
13. (b) Bentley, D. J.; Moody, C. J. Org. Biomol. Chem. 2004, 2, 3545.
14. (c) Harrison, J. R.; Moody, C. J. Tetrahedron Lett. 2003, 44, 5189.
15. (d) Comber, M. F.; Moody, C. J. Synthesis 1992, 731.
16. Yoshikawa, K.; Tao, S.; Arihara, S. J. Nat. Prod. 2000, 63, 540.
17. Castle, S. L.; Srikanth, G. S. C. Org. Lett. 2003, 5, 3611.
18. He, L.; Yang, L.; Castle, S. L. Org. Lett. 2006, 8, 1165.
19. Ma, B.; Litvinov, D. M.; He, L.; Banerjee, B.; Castle, S. L. Angew. Chem., Int. Ed. 2009, 48, 6104.
20. (a) Zhang, Y.; Wada, T.; Sasabe, H. Tetrahedron Lett. 1996, 37, 5909.
21. (b) Chrétien, F.; Khaldi, M.; Chapleur, Y. Tetrahedron Lett. 1997, 38, 5977.
22. For a review of radical conjugate additions, see: Srikanth, G. S. C.; Castle, S. L. Tetrahedron 2005, 61, 10377.
23. Although we are unaware of any pKa measurements of R-nitroacetamides, the pKa of methyl nitroacetate in H2O is 5.58. Bernasconi, C. F.; Pérez-Lorenzo, M.; Brown, S. D. J. Org. Chem. 2007, 72, 4416.
24. Srikanth, G. S. C.; Castle, S. L. Org. Lett. 2004, 6, 449.
25. Ma, B.; Litvinov, D. N.; Srikanth, G. S. C.; Castle, S. L. Synthesis 2006, 3291.
26. For a review of Lewis acid promoted radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
27. (a) Moody, C. J.; Shah, P. J. Chem. Soc., Perkin Trans. 1 1989, 2463.
28. (b) Kim, M.; Vedejs, E. J. Org. Chem. 2004, 69, 7262.
29. Jew, S.-s.; Yoo, M.-S.; Jeong, B.-S.; Park, I.-Y.; Park, H.-g. Org. Lett. 2002, 4, 4245.
30. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
31. Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
32. (a) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963.
33. (b) Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 4607.
34. (a) Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378.
35. (b) Nicolaou, K. C.; Zak, M.; Safina, B. S.; Estrada, A. A.; Lee, S. H.; Nevalainen, M. J. Am. Chem. Soc. 2005, 127, 11176.
36. Braslau, R.; Anderson, M. O.; Rivera, F.; Jimenez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513.
37. (a) McFadyen, J. S.; Stevens, T. S. J. Chem. Soc. 1936, 584.
38. (b) Matin, S. B.; Craig, J. C.; Chan, R. P. K. J. Org. Chem. 1974, 39, 2285.
39. (a) Rapoport, H.; Holden, K. G. J. Am. Chem. Soc. 1960, 82, 5510.
40. (c) Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405.
41. Casimir, J. R.; Guichard, G.; Briand, J.-P. J. Org. Chem. 2002, 67, 3764.
42. (a) Bergman, J.; Engqvist, R.; Stålhandske, C.; Wallberg, H. Tetrahedron 2003, 59, 1033.
43. (b) Engqvist, R.; Bergman, J. Tetrahedron 2003, 59, 9649.
44. (c) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
45. (a) Birkofer, L.; Bierstein, E.; Ritter, F. Chem. Ber. 1961, 94, 821.
46. (b) Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870.
47. (c) Coleman, R. S.; Shah, J. A. Synthesis 1999, 1399.
48. (a) Manjunatha, S. G.; Chittari, P.; Rajappa, S. Helv. Chim. Acta 1991, 74, 1071.
49. (b) Manjunatha, S. G.; Reddy, K. V.; Rajappa, S. Tetrahedron Lett. 1990, 31, 1327.
50. Fornicola, R. S.; Oblinger, E.; Montgomery, J. J. Org. Chem. 1998, 63, 3528.
51. Sui, Y.; Liu, L.; Zhao, J.-L.; Wang, D.; Chen, Y.-J. Tetrahedron Lett. 2007, 48, 3779.
52. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K. Eur. J. Org. Chem. 2004, 546.
53. Sinha, A. K.; Sharma, A.; Joshi, B. P. Tetrahedron 2007, 63, 960.
54. Deb, M. L.; Bhuyan, P. J. Tetrahedron Lett. 2005, 46, 6453.
55. Wang, X.-S.; Zeng, Z.-S.; Shi, D.-Q.; Wei, X.-Y.; Zong, Z.-M. Youji Huaxue 2005, 25, 1138.
56. Paquette, L. A.; Collado, I.; Purdie, M. J. Am. Chem. Soc. 1998, 120, 2553.
57. Witiak, D. T.; Loper, J. T.; Ananthan, S.; Almerico, A. M.; Verhoef, V. L.; Filppi, J. A. J. Med. Chem. 1989, 32, 1636.
58. Abaee, M. S.; Mojtahedi, M. M.; Zahedi, M. M.; Sharifi, R.; Khavasi, H. Synthesis 2007, 3339.
59. He, L.; Srikanth, G. S. C.; Castle, S. L. J. Org. Chem. 2005, 70, 8140.
60. (a) Lee, J. G.; Choi, K. I.; Koh, H. Y.; Kim, Y.; Kang, Y.; Cho, Y. S. Synthesis 2001, 81.
61. (b) Singh, V.; Kanojiya, S.; Batra, S. Tetrahedron 2006, 62, 10100.
62. Gowda, D. C.; Mahesh, B.; Gowda, S. Indian J. Chem., Sect. B 2001, 40B, 75.
63. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721.
64. Handa, S.; Gnanadesikan, V.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900.
65. (a) Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1991, 32, 1699.
66. (b) Sturgess, M. A.; Yarberry, D. J. Tetrahedron Lett. 1993, 34, 4743.
67. (a) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997,62, 6454.
68. (b) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417.
69. (c) Iserloh, U.; Oderaotoshi, Y.; Kanemasa, S.; Curran, D. P. Org. Synth. 2003, 80, 46.
70. Banerjee, B.; Capps, S. G.; Kang, J.; Robinson, J. W.; Castle, S. L. J. Org. Chem. 2008, 73, 8973.
71. Boeckman, R. K., Jr.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
72. See the Supporting Information for details.
73. Fields, C. G.; Fields, G. B. Tetrahedron Lett. 1993, 34, 6661.
74. Regarding the NOE correlations observed with natural celogentin C, the text of ref 1 is in error. The correct data can be located in Table 3 and on the NOESY spectrum given in the Supporting Information. This discrepancy caused us previously to erroneously conclude that our model right-hand ring of celogentin C was the unnatural atropisomer (see ref 13).