Tandem Enyne Metathesis-Diels-Alder Reaction for Construction of Natural Product Frameworks

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 2084-2093

  Rosillo, Marta ^a   Domínguez, Gema ^a   Casarrubios, Luis ^a,c   Amador, Ulises ^b   Pérez Castells, Javier ^a  

^a UNIVERSIDAD SAN PABLO CEU   (Spain)

^b Fac Cie Experimentales Y la Salud   (Spain)

^c ELI LILLY AND COMPANY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM;

METATHESIS REACTIONS; POLYCYCLIC STRUCTURES;

SUBSTITUTION REACTIONS;

ALKADIENE; CARBENE; CHEMICAL COMPOUND; ENAMINE; ENYNE; INDOLE DERIVATIVE; LEWIS ACID; NATURAL PRODUCT; RUTHENIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLINDOLE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ALKADIENES; ALKYNES; BIOLOGICAL FACTORS; CATALYSIS; HYDROCARBONS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MOLECULAR STRUCTURE; RUTHENIUM; SOLVENTS; VINYL COMPOUNDS;

EID: 12144288301     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0356311     Document Type: Article

References (66)

1. For recent reviews on the olefin metathesis reaction, see: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
2. (b) Schrock, R. R. Tetrahedron 1999, 55, 8141.
3. (c) Wright, D. L. Curr. Org. Chem. 1999, 3, 211.
4. (d) Philips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
5. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
6. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
7. (g) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
8. For recent reviews on enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
9. (b) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
10. Recent references on intramolecular ruthenium-based enyne metathesis: (a) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
11. (b) Duboc, R.; Henaut, C.; Savignac, M.; Genêt, J.-P. Bhatnagar, N. Tetrahedron Lett. 2001, 42, 2461.
12. (c) Rückert, A.; Eisele, D.; Blechert, S. Tetrahedron Lett. 2001, 42, 5245.
13. (d) Yao, Q. Org. Lett. 2001, 3, 2069.
14. (e) Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787.
15. (f) Marco-Contelles, J.; Arroyo, N.; Ruiz-Caro, J. Synlett 2001, 652.
16. (g) Ackermann, L.; Bruneau, C.; Dixneuf, P. H. Synlett 2001, 397.
17. (h) Clark, J. S. Townsend, R. J.; Blake, A. J.; Teat, S. J.; Johns, A. Tetrahedron Lett. 2001, 42, 3235.
18. (i) Bentz, D.; Laschat, S. Synthesis 2000, 1766.
19. (j) Smulik, J. A.; Diver, S. T. J. Org. Chem. 2000, 65, 1788.
20. (k) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
21. (l) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465.
22. (m) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato, Y. Org. Lett. 2000, 2, 543.
23. (n) Kotha, S.; Sreenivasachary, N. Chem. Commun. 2000, 503.
24. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
25. (a) Synthesis of 2: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
26. (b) Synthesis of 3: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
27. Wakamatsu, H.; Blechert, S. Angew. Chem, Int. Ed. 2002, 41, 794
28. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
29. (c) Van Veldhuizen, J. J.; Garber, S. B.; Kingbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
30. See: (a) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
31. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749.
32. (c) Aagaard, O. M.; Meier, R. J.; Buda, F. J. Am. Chem. Soc. 1998, 120, 7174.
33. Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277.
34. Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258.
35. For a recent review on olefin cross metathesis see: Connon, S. J.; Blechert, S. Angew. Chem, Int. Ed. 2003, 42, 1900.
36. See: (a) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
37. (b) Moreno-Mañas, M.; Pleixats, R.; Santamaria, A. Synlett 2001, 1784 and ref 3i. For a recent example of a three-component tandem metathesis/Diels-Alder reaction, see: Lee, H.-Y.; Kim, H. Y.; Tae, H.; Kim, B. G.; Lee, J. Org. Lett. 2003, 5, 3439.
38. (b) Moreno-Mañas, M.; Pleixats, R.; Santamaria, A. Synlett 2001, 1784 and ref 3i. For a recent example of a three-component tandem metathesis/Diels-Alder reaction, see: Lee, H.-Y.; Kim, H. Y.; Tae, H.; Kim, B. G.; Lee, J. Org. Lett. 2003, 5, 3439.
39. Lane, C.; Snieckus, V. Synlett 2000, 1294.
40. Schurer, S. C.; Blechert, S. Tetrahedron Lett. 1999, 40, 1877.
41. See: (a) Banti, D.; North, M. Tetrahedron Lett. 2002, 43, 1561.
42. (b) Guo, H.; Madhushaw, R. J.; Shen, F.-M.; Liu, R.-S. Tetrahedron 2002, 58, 5627.
43. (c) Schürer, S. C.; Blechert, S. Chem. Commun. 1999, 1203.
44. For a preliminary communication of part of this work, see: Rosillo, M.; Casarrubios, L.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2001, 42, 7029.
45. Keusenkothen, P. F.; Smith, M. B. Tetrahedron Lett. 1992, 48, 2977.
46. (a) Maishal, T. K.; Sinha-Mahapatra, D. K.; Paranjape, K.; Sarkar, A. Tetrahedron Lett. 2002, 43, 2263.
47. (b) Gurjar, M. K.; Yakambram, P. Tetrahedron Lett. 2001, 42, 3633.
48. (c) Paquette, L. A.; Efremov, I. J. Am. Chem. Soc. 2001, 123, 4492.
49. (d) Davoille, R. J.; Rutherford, D. T.; Christie, S. D. R. Tetrahedron Lett. 2000, 41, 1255.
50. (e) Krikstolaityte, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595. In intermolecular enyne reactions coordination effects of oxygen atoms have also been identified sometimes with an accelerating result. See: Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235. Other authors circumvented this problem with adequate choice of the catalyst. Smulik, J. A.; Diver, S. T. Org. Lett. 2000, 2, 2271.
51. (e) Krikstolaityte, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595. In intermolecular enyne reactions coordination effects of oxygen atoms have also been identified sometimes with an accelerating result. See: Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235. Other authors circumvented this problem with adequate choice of the catalyst. Smulik, J. A.; Diver, S. T. Org. Lett. 2000, 2, 2271.
52. (e) Krikstolaityte, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595. In intermolecular enyne reactions coordination effects of oxygen atoms have also been identified sometimes with an accelerating result. See: Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235. Other authors circumvented this problem with adequate choice of the catalyst. Smulik, J. A.; Diver, S. T. Org. Lett. 2000, 2, 2271.
53. Compound 30 was obtained from 2-iodoacetanilide by Stille reaction with tributylvinyltin and subsequent propargylation of the amide. See Supporting Information for details.
54. (a) Schuster, T.; Kurz, M.; Göbel, M. W. J. Org. Chem. 2000, 65, 1697.
55. (b) García Ruano, J. L.; Alemparte, C.; Martín Castro, A.; Adams, H.; Rodríguez Ramos, J. J. Org. Chem. 2000, 65, 7938.
56. This would imply a nonmetathetic behavior of the ruthenium complex. See: Alcaide, B.; Almendros, P. Chem. Eur. J. 2003, 9, 1258.
57. The only example of indole synthesis using olefin RCM: Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem, Int. Ed. 2002, 41, 4732.
58. Domínguez, G.; Casarrubios, L.; Rodriguez-Noriega, J.; Pérez-Castells, J. Helv. Chim. Acta 2002, 85, 2856.
59. See Supporting Information for data on the synthesis of compounds 43 and 44.
60. See Supporting Information for complete spectra of these reactions and of the rest of the Table 3 reactions.
61. We thank one of the referees of this work for useful proposals on these mechanistic aspects.
62. Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606.
63. These ruthenium metalacycles have been proposed in cyclizations catalysed by noncarbene ruthenium(II) species: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714.
64. (b) Chatani, N.; Kataoka, K.; Murai, S. J. Am. Chem. Soc. 1998, 120, 9104.
65. Hansen, H. D.; Nelson, J. H. Organometallics 2000, 19, 4740.
66. Cetinkaya, B.; Demir, S.; Ozdemir, I.; Toupet, L.; Semeril, D.; Bruneau, C.; Dixneuf, P. H. New J. Chem. 2001, 25, 519.