Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine

Angewandte Chemie - International Edition

Volumn 47, Issue 46, 2008, Pages 8885-8888

  Hudon, Jonathan ^a   Cernak, Timothy A ^a   Ashenhurst, James A ^a   Gleason, James L ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Cycloaddition; Diels Alder reaction; Sigmatropic shift; Synthetic methods

Indexed keywords

AMINES; CHEMICAL REACTIONS; CHEMICAL REACTIVITY; CHEMICAL STABILITY; FRICTION MATERIALS; ORGANIC COMPOUNDS; SILANES;

BUTYLDIMETHYLSILYL; CHEMICAL EQUATIONS; CYCLOPENTADIENES; DIELS-ALDER REACTION; MARINE ALKALOIDS; SIGMATROPIC SHIFT; SYNTHESIS OF; SYNTHETIC METHODS;

SYNTHESIS (CHEMICAL);

EID: 57349170350     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803344     Document Type: Article

References (53)

1. a) E. J. Corey, N. M. Weinshenker, T. K. Schaaf, W. Huber, J. Am. Chem. Soc. 1969, 91, 5675;
2. for a recent exquisite example which takes advantage of differential reactivity of 1- and 2-substituted cyclopentadienes, see: b) P. Li, J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9534;
3. c) J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9536.
4. For other examples of 5-substituted cyclopentadienes in Diels-Alder cycloaddition reactions, see: a) J. E. Letourneau, M. A. Wellman, D. J. Burnell, J. Org. Chem. 1997, 62, 7272;
5. b) M. A. Wellman, L. C. Burry, J. E. Letourneau, J. N. Bridson, D. O. Miller, D. J. Burnell, J. Org. Chem. 1997, 62, 939;
6. c) S. B. King, B. Ganem, J. Am. Chem. Soc. 1994, 116, 562;
7. d) B. K. Goering, B. Ganem, Tetrahedron Lett. 1994, 35, 6997;
8. e) M. A. McClinton, V. Sik, J. Chem. Soc. Perkin Trans. 1 1992, 1891;
9. f) M. Franck-Neumann, M. Sedrati, Tetrahedron Lett. 1983, 24, 1391;
10. g) R. Breslow, J. M. Hoffman, Jr., C. Perchonock, Tetrahedron Lett. 1973, 14, 3723;
11. h) S. Winstein, M. Shatavsky, C. Norton, R. B. Woodward, J. Am. Chem. Soc. 1955, 77, 4183.
12. a) G. Kresze, G. Schulz, H. Walz, Ann. Chem. 1963, 45, 666;
13. b) V. A. Mironov, E. V. Sobolev, A. N. Elizarova, Tetrahedron 1963, 19, 1939;
14. c) D. McNeil, B. R. Vogt, J. J. Sudol, S. Theodoropulos, E. Hedaya, J. Am. Chem. Soc. 1974, 96, 4673; exception are 5-halocyclopentadienes which rearrange at slower rates, see: Ref. [2g].
15. For examples of 6-substituted fulvenes, see: a) E. D. Brown, R. Clarkson, T. J. Leeney, G. E. Robinson, Chem. Commun. 1974, 642;
16. b) P. Yates, J. P. Lokensgard, Synth. Commun. 1975, 5, 37;
17. for intramolecular trapping, see: c) M. Ohkita, H. Kawai, T. Tsuji, J. Chem. Soc. Perkin Trans. 1 2002, 366;
18. for examples of spirobicyclo-[4.2.0]heptadienes where a [1,5]-sigmatropic shift is not possible, see: d) E. J. Corey, C. S. Shiner, R. P. Volante, C. R. Cyr, Tetrahedron Lett. 1975, 16, 1161;
19. e) S. K. Attah-Poku, G. Gallacher, A. S. Ng, L. E. B. Taylor, S. J. Alward, A. G. Fallis, Tetrahedron Lett. 1983, 24, 677;
20. f) A. G. González, J. Darias, F. Diaz, Tetrahedron Lett. 1984, 25, 2697;
21. g) J. T. Starr, G. Koch, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 8793.
22. a) J. S. Bajorek, R. Battaglia, G. Pratt, J. K. Sutherland, J. Chem. Soc. Perkin Trans. 1 1974, 1243;
23. b) E. A. Saville-Stones, R. M. Turner, S. D. Lindell, N. S. Jennings, J. C. Head, D. S. Carver, Tetrahedron 1994, 50, 6695.
24. J. M. Bobbitt, J. Org. Chem. 1998, 63, 9367;
25. Caution, the perchlorate salt is reported to be explosive, but it can be replaced by the tetrafluoroborate salt, see: J. M. Bobbitt, Chem. Eng. News 1999, 29, 6.
26. For silylation of 2-cyclopenten-1-one, see: H. Plenio, C. Aberle, Organometallics 1997, 16, 5950.
27. S. MacLean, P. Haynes, Tetrahedron 1965, 21, 2329.
28. Methyl groups at either the 1- or 2-position have been reported to slow down [1,5]-sigmatropic shifts in 5-substituted cyclopentadienes, but their preparation is problematic, see Ref. [8] and a) S. McLean, P. Haynes, Tetrahedron 1965, 21, 2313;
29. electron withdrawing groups have been reported to accelerate [1,5]-hydrogen shifts, see: b) W. H. Okamura, G.-Y. Shen, R. Tapia, J. Am. Chem. Soc. 1986, 108, 5018.
30. Gaussian 03 (Revision C.02), M. J. Frisch, et al. Gaussian, Inc., Wallingford, CT, 2004.
31. Calculations at the MPW1K/6-31G* level produced similar results, see: G. R. Shelton, D. A. Hrovat, W. T. Bordon, J. Am. Chem. Soc. 2007, 129, 164.
32. 3J(H,C) coupling constants. In contrast to simple 5-substituted cyclopentadienes (see Ref. [2a]), no cycloadducts arising from addition syn to the 5-silyloxymethyl group were observed.
33. 2 were not compatible and resulted in significant diene decomposition; for related stability issues, see: T. J. Reddy, V. H. Rawal, Org. Lett. 2000, 2, 2711.
34. a) D. M. Hodgson, J. Witherington, B. A. Moloney, J. Chem. Soc. Perkin Trans. 1 1994, 3373;
35. b) D. M. Hodgson, A. R. Gibbs, M. G. B. Drew, J. Chem. Soc. Perkin Trans. 1 1999, 3579-3590.
36. 3 induced isomerization of 4.
37. a) R. B. Kinnel, H.-P. Gehrken, P. J. Scheuer, J. Am. Chem. Soc. 1993, 115, 3376;
38. b) R. B. Kinnel, H.-P. Gehrken, R. Swali, G. Skoropowski, P. J. Scheuer, J. Org. Chem. 1998, 63, 3281.
39. For recent reviews of synthetic studies towards palau'amine, see: a) D. E. N. Jacquot, T. Lindel, Curr. Org. Chem. 2005, 9, 1551;
40. b) H. Hoffmann, T. Lindel, Synthesis 2003, 1753;
41. c) Z. Jin, Nat. Prod. Rep. 2006, 23, 464.
42. a) A. Grube, M. Köck, Angew. Chem. 2007, 119, 2372;
43. Angew. Chem. Int. Ed. 2007, 46, 2320;
44. b) M. S. Buchanan, A. R. Carroll, R. Addelpalli, V. M. Avery, J. N. A. Hooper, R. J. Quinn, J. Org. Chem. 2007, 72, 2309;
45. c) H. Kobayashi, K. Kitamura, K. Nagai, Y. Nakao, N. Fusetani, R. W. M. van Soest, S. Matsunaga, Tetrahedron Lett. 2007, 48, 2127;
46. d) M. S. Buchanan, A. R. Carroll, R. J. Quinn, Tetrahedron Lett. 2007, 48, 4573;
47. e) B. A. Lanman, L. E. Overman, R. Paulini, N. S. White, J. Am. Chem. Soc. 2007, 129, 12896.
48. After the submission of this paper, Gin and co-workers reported the synthesis of both cyclopentane stereoarrays in 14 a and 14b using a Diels-Alder cycloaddition followed by sigmatropic rearrangement, see: M. S. Bultman, J. Ma, D. Y. Gin, Angew. Chem. 2008, 120, 6927;
49. Angew. Chem. Int. Ed. 2008, 47, 6821.
50. For model studies using cyclopentadiene in place of 6, see: T. A. Cernak, J. L. Gleason, J. Org. Chem. 2008, 73, 102.
51. Carreira and co-workers have reported a route to the axinellimine core, which contains the same configuration as the E ring of 14b. They used Diels-Alder cycloaddition of a spiro fused cyclopentadiene followed by ozonolysis and chlorinative decarbonylation, see Ref. [4g].
52. J. M. Bland, C. H. Stammer, K. I. Varughese, J. Org. Chem. 1984, 49, 1634.
53. For the application of a [6+4] tropone cycloaddition in the synthesis of the core of CP-225,917, see: J. A. Ashenhurst, J. L. Gleason, Tetrahedron Lett. 2008, 49, 504.