The second total synthesis of diazonamide A

Angewandte Chemie - International Edition

Volumn 42, Issue 15, 2003, Pages 1753-1758

  Nicolaou, K C ^a,b   Bheema Rao, Paraselli ^a,b   Hao, Junliang ^a,b   Reddy, Mali Venkat ^a,b   Rassias, Gerasimos ^a,b   Huang, Xianhai ^a,b   Chen, David Y K ^a,b   Snyder, Scott A ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Domino reactions; Macrocycles; Natural products; Samarium; Total synthesis

Indexed keywords

OXIDATION; PALLADIUM; SYNTHESIS (CHEMICAL);

DIAZONAMIDE;

AROMATIC COMPOUNDS;

AMIDE; AMINO ACID DERIVATIVE; ANTINEOPLASTIC AGENT; BENZYL DERIVATIVE; DIAZONAMIDE A; HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CHLORINATION; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; ROBINSON ANNULATION; STRUCTURE ANALYSIS;

BIOLOGICAL FACTORS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; IODIDES; MOLECULAR STRUCTURE; OXAZOLES; SAMARIUM; STEREOISOMERISM;

EID: 0037541199     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351112     Document Type: Article

References (66)

1. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
2. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
3. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
4. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
5. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
6. For discussions of this topic in the context of total synthesis, see examples in the following: a) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; b) K. C. Nicolaou, S. A. Snyder, T Montagnon, G. A. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773; Angew. Chem. Int. Ed. 2002, 41, 1668-1698; c) K. C. Nicolaou, P. S. Baran, Angew. Chem. 2002, 114, 2800-2843; Angew. Chem. Int. Ed. 2002, 41, 2678-2720.
7. For the isolation and original structural assignments, see: a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304; for the synthesis of the originally proposed structure and revision of the structure of diazonamide A, see: b) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. 2001, 113, 4901-4906; Angew. Chem. Int. Ed. 2001, 40, 4765-4770; c) J. Li, A. W. G. Burgett, L. Esser, C. Amezcua, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909; Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
8. For the isolation and original structural assignments, see: a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304; for the synthesis of the originally proposed structure and revision of the structure of diazonamide A, see: b) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. 2001, 113, 4901-4906; Angew. Chem. Int. Ed. 2001, 40, 4765-4770; c) J. Li, A. W. G. Burgett, L. Esser, C. Amezcua, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909; Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
9. For the isolation and original structural assignments, see: a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304; for the synthesis of the originally proposed structure and revision of the structure of diazonamide A, see: b) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. 2001, 113, 4901-4906; Angew. Chem. Int. Ed. 2001, 40, 4765-4770; c) J. Li, A. W. G. Burgett, L. Esser, C. Amezcua, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909; Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
10. For the isolation and original structural assignments, see: a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304; for the synthesis of the originally proposed structure and revision of the structure of diazonamide A, see: b) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. 2001, 113, 4901-4906; Angew. Chem. Int. Ed. 2001, 40, 4765-4770; c) J. Li, A. W. G. Burgett, L. Esser, C. Amezcua, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909; Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
11. For the isolation and original structural assignments, see: a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304; for the synthesis of the originally proposed structure and revision of the structure of diazonamide A, see: b) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. 2001, 113, 4901-4906; Angew. Chem. Int. Ed. 2001, 40, 4765-4770; c) J. Li, A. W. G. Burgett, L. Esser, C. Amezcua, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909; Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
12. For highlights of previous synthetic studies towards the diazonamides, see: a) V. Wittmann, Nachr. Chem. 2002, 50, 477-482; b) T. Ritter, E. M. Carreira, Angew. Chem. 2002, 114, 2601-2606; Angew. Chem. Int. Ed. 2002, 41, 2489-2495.
13. For highlights of previous synthetic studies towards the diazonamides, see: a) V. Wittmann, Nachr. Chem. 2002, 50, 477-482; b) T. Ritter, E. M. Carreira, Angew. Chem. 2002, 114, 2601-2606; Angew. Chem. Int. Ed. 2002, 41, 2489-2495.
14. For highlights of previous synthetic studies towards the diazonamides, see: a) V. Wittmann, Nachr. Chem. 2002, 50, 477-482; b) T. Ritter, E. M. Carreira, Angew. Chem. 2002, 114, 2601-2606; Angew. Chem. Int. Ed. 2002, 41, 2489-2495.
15. a) J. Li, X. Chen, A. W. G. Burgett, P. G. Harran, Angew. Chem. 2001, 113, 2754-2757; Angew. Chem. Int. Ed. 2001, 40, 2682-2685;
16. a) J. Li, X. Chen, A. W. G. Burgett, P. G. Harran, Angew. Chem. 2001, 113, 2754-2757; Angew. Chem. Int. Ed. 2001, 40, 2682-2685;
17. b) X. Chen, L. Esser, P. G. Harran, Angew. Chem. 2000, 112, 967-970; Angew. Chem. Int. Ed. 2000, 39, 937-940;
18. b) X. Chen, L. Esser, P. G. Harran, Angew. Chem. 2000, 112, 967-970; Angew. Chem. Int. Ed. 2000, 39, 937-940;
19. c) S. Jeong, X. Chen, P. G. Harran, J. Org. Chem. 1998, 63, 8640-8641.
20. a) E. Vedejs, M. A. Zajac, Org. Lett. 2001, 3, 2451-2454;
21. b) E. Vedejs, J. Wang, Org. Lett. 2000, 2, 1031-1032;
22. c) E. Vedejs, D. A. Barba, Org. Lett. 2000, 2, 1033-1035.
23. a) P. Wipf, J.-L. Methot, Org. Lett. 2001, 3, 1261-1264;
24. b) P. Wipf, F. Yokokawa, Tetrahedron Lett. 1998, 39, 2223-2226.
25. a) J. D. Kreisberg, P. Magnus, E. G. McIver, Tetrahedron Lett. 2001, 42, 627-629;
26. b) P. Magnus, E. G. McIver, Tetrahedron Lett. 2000, 41, 831-834;
27. c) F. Chan, P. Magnus, E.G. McIver, Tetrahedron Lett. 2000, 41, 835-838;
28. d) P. Magnus, J. D. Kreisberg, Tetrahedron Lett. 1999, 40, 451-454.
29. D. E. Fuerst, B. M. Stoltz, J. L. Wood, Org. Lett. 2000, 2, 3521-3523.
30. a) S. Schley, A. Radspieler, G. Christoph, J. Liebscher, Eur. J. Org. Chem. 2002, 369-374;
31. b) A. Radspieler, J. Liebscher, Synthesis 2001, 745-750.
32. a) F. Lach, C. J. Moody, Tetrahedron Lett. 2000, 41, 6893-6896;
33. b) M. C. Bagley, S. L. Hind, C. J. Moody, Tetrahedron Lett. 2000, 41, 6897-6900;
34. c) M. C. Bagley, C. J. Moody, A. G. Pepper, Tetrahedron Lett. 2000, 41, 6901-6904;
35. d) C. J. Moody, K. J. Doyle, M. C. Elliott, T. J. Mowlem, J. Chem. Soc. Perkin Trans. 1 1997, 2413-2419;
36. e) C. J. Moody, K. J. Doyle, M. C. Elliott, T. J. Mowlem, Pure Appl. Chem. 1994, 66, 2107-2110.
37. K. S. Feldman, K. J. Eastman, G. Lessene, Org. Lett. 2002, 4, 3524-3528.
38. a) H. C. Hang, E. Drotleff, G. I. Elliott, T. A. Ritsema, J. P. Konopelski, Synthesis 1999, 398-400;
39. b) J. P. Konopelski, J. M. Hottenroth, H. M. Oltra, E. A. Veliz, Z. C. Yang, Synlett 1996, 609-611.
40. A. Boto, M. Ling, G. Meek, G. Pattenden, Tetrahedron Lett. 1998, 39, 8167-8170.
41. K. C. Nicolaou, M. Bella, D. Y.-K. Chen, X. Huang, T. Ling, S. A. Snyder, Angew. Chem. 2002, 114, 3645-3649; Angew. Chem. Int. Ed. 2002, 41, 3495-3499.
42. K. C. Nicolaou, M. Bella, D. Y.-K. Chen, X. Huang, T. Ling, S. A. Snyder, Angew. Chem. 2002, 114, 3645-3649; Angew. Chem. Int. Ed. 2002, 41, 3495-3499.
43. a) K. C. Nicolaou, S. A. Snyder, K. B. Simonsen, A. E. Koumbis, Angew. Chem. 2000, 112, 3615-3620; Angew. Chem. Int. Ed. 2000, 39, 3473-3478;
44. a) K. C. Nicolaou, S. A. Snyder, K. B. Simonsen, A. E. Koumbis, Angew. Chem. 2000, 112, 3615-3620; Angew. Chem. Int. Ed. 2000, 39, 3473-3478;
45. b) K. C. Nicolaou, X. Huang, N. Giuseppone, P. Bheema Rao, M. Bella, M. V. Reddy, S. A. Snyder, Angew. Chem. 2001, 113, 4841-4845; Angew. Chem. Int. Ed. 2001, 40, 4705-4709.
46. b) K. C. Nicolaou, X. Huang, N. Giuseppone, P. Bheema Rao, M. Bella, M. V. Reddy, S. A. Snyder, Angew. Chem. 2001, 113, 4841-4845; Angew. Chem. Int. Ed. 2001, 40, 4705-4709.
47. T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508-7510.
48. This step was inspired by related work: D. A. Klumpp, K. Y. Yeung, G. K, Surya Prakash, G. A. Olah, J. Org. Chem. 1998, 63, 4481-4484, and references therein.
49. A. Padwa, D. Dehm, T. Oine, G. A. Lee, J. Am. Chem. Soc. 1975, 97, 1837-1845.
50. The presence of the C11 carbonyl group retarded Suzuki coupling with 6 and led to the loss of the hydroxymethyl function on several intermediates as a result of the same type of fragmentation discussed in reference [15 a] that afforded benzofuran products; for a productive use of this pathway, see: K. C. Nicolaou, S. A. Snyder, A. Bigot, J. A. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096.
51. The presence of the C11 carbonyl group retarded Suzuki coupling with 6 and led to the loss of the hydroxymethyl function on several intermediates as a result of the same type of fragmentation discussed in reference [15 a] that afforded benzofuran products; for a productive use of this pathway, see: K. C. Nicolaou, S. A. Snyder, A. Bigot, J. A. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096.
52. M. Nishiura, K. Katagiri, T. Imamoto, Bull. Chem. Soc. Jpn. 2001, 74, 1417-1424.
53. 2, such as our previously reported choice of HMPA (see reference [15 b]), did lead to the desired product, albeit in a lower yield.
54. 3: R. L. Dow, J. Org. Chem. 1990, 55, 386-388.
55. For examples of other conditions attempted to engender a Gabriel-Robinson dehydration, see: a) P. Wipf, C. P. Miller, J. Org. Chem. 1993, 58, 3604-3606; b) C. T. Brain, J. M. Paul, Synlett 1999, 1642-1644.
56. For examples of other conditions attempted to engender a Gabriel-Robinson dehydration, see: a) P. Wipf, C. P. Miller, J. Org. Chem. 1993, 58, 3604-3606; b) C. T. Brain, J. M. Paul, Synlett 1999, 1642-1644.
57. For numerous examples of challenging macrolactamizations, see: D. L. Boger, S. H. Kim, Y. Mori, J.-H. Weng, O. Rogel, S. L. Castle, J. J. McAtee, J. Am. Chem. Soc. 2001, 123, 1862-1871.
58. I), see: K. C. Nicolaou, C. W. Hummel, M. Nakada, K. Shibayama, E. N. Pitsinos, H. Saimoto, Y. Mizuno, K.-U. Baldenius, A. L. Smith, J. Am. Chem. Soc. 1993, 115, 7625-7635.
59. Although molecular models suggested the proximity of the reactive units, the steric hindrance within the system, in combination with the entropic penalties associated with the formation of a 12-membered ring with multiple elements of unsaturation from a far more flexible precursor, were the likely culprits that led to such recalcitrance.
60. For other syntheses that benefited from this reagent combination, see: a) K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622-2647; b) T. Hu, J. S. Panek, J. Org. Chem. 1999, 64, 3000-3001; c) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
61. For other syntheses that benefited from this reagent combination, see: a) K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622-2647; b) T. Hu, J. S. Panek, J. Org. Chem. 1999, 64, 3000-3001; c) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
62. For other syntheses that benefited from this reagent combination, see: a) K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622-2647; b) T. Hu, J. S. Panek, J. Org. Chem. 1999, 64, 3000-3001; c) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
63. For other syntheses that benefited from this reagent combination, see: a) K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622-2647; b) T. Hu, J. S. Panek, J. Org. Chem. 1999, 64, 3000-3001; c) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
64. This result, combined with the yields obtained for the macrocyclization steps in our first total synthesis, indicates that the presence of either macrocyclic unit does not favor the formation of the second, once again revealing the truly constrained and compact nature of diazonamide A.
65. Oxidative cleavage of benzyl ethers has been reported, although none of the substrates possessed nitrogen atoms; for an example, see: J. D. Prugh, C. S. Rooney, A. A. Deana, H. G. Ramiit, Tetrahedron Lett. 1985, 26, 2947.
66. +] found: 815.1778.