Total synthesis of (±)-strychnine via a [4 + 2]-cycloaddition/ rearrangement cascade

Organic Letters

Volumn 9, Issue 2, 2007, Pages 279-282

  Zhang, Hongjun ^a   Boonsombat, Jutatip ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; IODINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; PALLADIUM; STRYCHNINE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; FURANS; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM; STRYCHNINE; VINYL COMPOUNDS;

EID: 33846571401     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062728b     Document Type: Article

References (59)

1. For leading reviews of Strychnos alkaloids, see: (a) Bosch, J.; Bonjoch, J.; Amat, M. Alkaloids 1996, 48, 75 and references cited therein.
2. (b) Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455.
3. Creasey, W. A. In The Monoterpene Indole Alkaloids; Saxton, J. E., Ed.; Interscience: New York, 1983; p 800.
4. The biogenetic numbering is used for pentacyclic structures such as 1; see: Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508.
5. (a) Robinson, R. Experientia 1946, 2, 28.
6. (b) Holmes, H. L.; Openshaw, H. T.; Robinson, R. J. Chem. Soc. 1946, 908.
7. (c) Openshaw, H. T.; Robinson, R. Nature 1946, 157, 438.
8. Pelletier, P. J.; Caventou, J. B. Ann. Chim. Phys. 1818, 8, 323.
9. (a) Aprison, M. H. In Glycine Neurotransmission; Otterson, O. P., Strom-Mathisen, J., Eds.; Wiley: New York, 1990; pp 1-23.
10. (b) Grenningloh, G.; Rienitz, A.; Schmitt, B.; Methfessel, C.; Zensen, M.; Beyreuther, K.; Gundelfinger, E. D.; Betz, H. Nature 1987, 328, 215.
11. (c) Kleckner, N. W.; Dingledine, R. Science 1988, 241, 835.
12. Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. J. Am. Chem. Soc. 1954, 76, 4749.
13. Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. Tetrahedron 1963, 19, 247.
14. (a) Magnus, P.; Giles, M.; Bonnert, R.; Kim, C. S.; McQuire, L.; Merritt, A.; Vicker, N. J. Am. Chem. Soc. 1992, 114, 4403.
15. Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. J. Am. Chem. Soc. 1993, 115, 8116.
16. (b) Stork, G. Presented at the Ischia Advanced School of Organic Chemistry, Ischia Porto, Italy, September 21, 1992.
17. (c) Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1993, 115, 9293.
18. Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776.
19. (d) Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490.
20. Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9427.
21. (e) Rawal, V. H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685.
22. (f) Solé, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Angew. Chem., Int. Ed. 1999, 38, 395.
23. Solé, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Chem. - Eur. J. 2000, 6, 655.
24. (g) Eichberg, M. J.; Dorta, R. L.; Lamottke, K.; Vollhardt, K. P. C. Org. Lett. 2000, 2, 2479.
25. Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 2001, 123, 9324.
26. (h) Ito, M.; Clark, C. W.; Mortimore, M.; Goh, J. B.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 8003.
27. (i) Nakanishi, M.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1934.
28. Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801.
29. (j) Bodwell, G. J.; Li, J. Angew. Chem., Int. Ed. 2002, 41, 3261.
30. (k) Ohshima, T.; Xu, Y.; Takita, R.; Shimizu, S.; Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546.
31. Ohshima, T.; Xu, Y.; Takita, R.; Shibasaki, M. Tetrahedron 2004, 60, 9569.
32. (l) Kaburagi, Y.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2004, 126, 10246.
33. (a) Wang, Q.; Padwa, A. Org. Lett. 2004, 6, 2189.
34. (b) Padwa, A.; Ginn, J. D. J. Org. Chem. 2005, 70, 5197.
35. (c) Padwa, A.; Bur, S. K.; Zhang, H. J. Org. Chem. 2005, 70, 6833.
36. (d) Zhang, H.; Padwa, A. Org. Lett. 2006, 8, 247.
37. Prelog, V.; Battegay, J.; Taylor, W. I. Helv. Chim. Acta 1948, 31, 2244.
38. Anet, F. A. L.; Robinson, R. Chem. Ind. 1953, 245. See also ref 8a,c.
39. (a) Solé, D.; Peidró, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225.
40. (b) Solé, D.; Diaba, J.; Bonjoch, J. J. Org. Chem. 2003, 68, 5746.
41. (c) Bonjoch, J.; Diaba, F.; Puigbó, G.; Peidró, E.; Solé, D. Tetrahedron Lett. 2003, 44, 8387.
42. (d) Solé, D.; Urbaneja, X.; Bonjoch, J. Adv. Synth. Catal. 2004, 346, 1646.
43. (e) Solé, D.; Urbaneja, X.; Bonjoch, J. Org. Lett. 2005, 7, 5461.
44. For some other examples of intramolecular Pd-catalyzed vinylations, see: (a) Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
45. (b) Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Flippen-Anderson, J.; Liao, X.; Cook, J. M. J. Org. Chem. 2003, 68, 7565.
46. (a) Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem. 1998, 63, 5304.
47. (b) Bur, S. K.; Lynch, S. M.; Padwa, A. Org. Lett. 2002, 4, 473.
48. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
49. Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
50. (a) Young, F. G.; Frostick, F. C.; Sanderson, J. J.; Hauser, C. R. J. Am. Chem. Soc. 1950, 72, 3635.
51. (b) Mao, C.-L.; Frostick, F. C.; Man, E. H.; Manyik, R. M.; Wells, R. L.; Hauser, C. R. J. Org. Chem. 1969, 34, 1425.
52. Attempts to introduce the vinyl iodide moiety earlier in the synthesis were unsuccessful due to the competitive loss of the iodo group during the reduction step.
53. The synthesis of the required allylic bromide is described in the Supporting Information.
54. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
55. The DMP group was selected as it was readily removed under the acidic conditions employed in the hydrolysis of 10 to the Wieland-Gumlich aldehyde (6) (see Scheme 5).
56. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
57. A similar approach was successfully employed in a synthesis of strychnopivotine (2), and this will be described at a later date.
58. Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1979, 3099.
59. Patel, D. V.; Schmidt, R. J.; Gordon, E. M. J. Org. Chem. 1992, 57, 7143.