Total synthesis of (-)-corynantheidine by nickel-catalyzed carboxylative cyclization of enynes

European Journal of Organic Chemistry

Volumn , Issue 14, 2011, Pages 2606-2609

  Mizuno, Takashi ^a   Oonishi, Yoshihiro ^a   Takimoto, Masanori ^a,b   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

Carbon dioxide fixation; Enynes; Nickel; Total synthesis

Indexed keywords

EID: 79955438844     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100147     Document Type: Article

References (45)

1. For reviews, see:, H. Arakawa, M. Aresta, J. N. Armor, M. A. Barteau, E. J. Beckman, A. T. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K. Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A. Goddard, W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E. Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas, R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D. Schmidt, A. Sen, G. A. Somorjai, P. Stair, B. R. Stults, W. Tumas, Chem. Rev. 2001, 101, 953.
2. P. Braunstein, D. Matt, D. Nobel, Chem. Rev. 1988, 88, 747.
3. D. H. Gibson, Chem. Rev. 1996, 96, 2063.
4. X. Yin, J. R. Moss, Coord. Chem. Rev. 1999, 181, 27.
5. T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365.
6. M. Mori, Eur. J. Org. Chem. 2007, 4981.
7. A. Correa, R. Martin, Angew. Chem. 2009, 121, 6317; Angew. Chem. Int. Ed. 2009, 48, 6201.
8. A. Correa, R. Martin, Angew. Chem. Int. Ed. 2009, 48, 6201.
9. Z. Hou, T. Ohishi in Comprehensive Organometallic Chemistry III (Eds.:, R. H. Crabtree, D. M. P. Mingos, I. Ojima), Elsevier, Oxford, 2007, vol. 10, pp. 537-555.
10. For recent representative examples, see
11. K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706.
12. G. E. Greco, B. L. Gleason, T. A. Lowery, M. J. Kier, L. B. Hollander, S. A. Gibbs, A. D. Worthy, Org. Lett. 2007, 9, 3817.
13. J. Takaya, S. Tadami, K. Ukai, N. Iwasawa, Org. Lett. 2008, 10, 2697.
14. T. Ohishi, M. Nishiura, Z. Hou, Angew. Chem. 2008, 120, 5876; Angew. Chem. Int. Ed. 2008, 47, 5792.
15. H. Ochiai, M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 2681.
16. C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 7826.
17. N. Eghbali, J. Eddy, P. T. Anastas, J. Org. Chem. 2008, 73, 6932.
18. J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2008, 130, 15254.
19. K. Kobayashi, Y. Kondo, Org. Lett. 2009, 11, 2035.
20. A. Metzger, S. Bernhardt, G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2010, 49, 4665.
21. I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858.
22. O. Vechorkin, N. Hirt, X. Hu, Org. Lett. 2010, 12, 3567.
23. M. Takimoto, T. Mizuno, Y. Sato, M. Mori, Tetrahedron Lett. 2005, 46, 5173.
24. M. Takimoto, T. Mizuno, M. Mori, Y. Sato, Tetrahedron 2006, 62, 7589.
25. For a review of nickel-mediated carboxylations, see:, M. Takimoto, M. Mori in Modern Organonickel Chemistry (Ed.:, Y. Tamaru), Wiley-VCH, Weinheim, 2005, pp. 205-223.
26. For partial and total syntheses of (±)-corynantheidine, see
27. J. A. Weisbach, J. L. Kirkpatrick, K. R. Williams, E. L. Anderson, N. C. Yim, B. Douglas, Tetrahedron Lett. 1965, 6, 3457.
28. E. Wenkert, K. G. Dave, R. G. Lewis, P. W. Sprague, J. Am. Chem. Soc. 1967, 89, 6741.
29. C. Szántay, M. Bárczai-Beke, Chem. Ber. 1969, 102, 3963.
30. R. T. Brown, C. L. Chapple, A. A. Charalambides, J. Chem. Soc., Chem. Commun. 1974, 756.
31. E. E. van Tamelen, C. Dorschel, Bioorg. Chem. 1976, 5, 203.
32. S. Sakai, N. Shinma, Chem. Pharm. Bull. 1978, 26, 2596.
33. M. Lounasmaa, R. Jokela, C. Laine, P. Hanhinen, Tetrahedron Lett. 1995, 36, 8687.
34. For formal syntheses of (-)-corynantheidine, see
35. R. L. Beard, A. I. Meyers, J. Org. Chem. 1991, 56, 2091.
36. Y. Li, T. Kobayashi, S. Katsumura, Tetrahedron Lett. 2009, 50, 4482 for the first total synthesis of (-)-corynantheidine, see
37. S. Yu, O. M. Berner, J. M. Cook, J. Am. Chem. Soc. 2000, 122, 7827.
38. P. D. Bailey, S. P. Hollinshead, N. R. McLay, Tetrahedron Lett. 1987, 28, 5177.
39. P. D. Bailey, K. M. Morgan, J. Chem. Soc. Perkin Trans. 1 2000, 3578.
40. 13C NMR spectroscopy, see:, F. Ungemach, S. R. Weber, M. DiPierro, O. Campos, C. P. Mokry, J. M. Cook, J. V. Silverton, J. Am. Chem. Soc. 1980, 102, 6976.
41. 0 complex has been isolated and characterized, see
42. 0 complex, whose structure was characterized to be a cyclic O-nickel enolate form, see
43. K. K. D. Amarasinghe, S. K. Chowdhury, M. J. Heeg, J. Montgomery, Organometallics 2001, 20, 370.
44. H. P. Hratchian, S. K. Chowdhury, V. M. Gutiérrez-García, K. K. D. Amarasinghe, M. J. Heeg, H. B. Schlegel, J. Montgomery, Organometallics 2004, 23, 4636.
45. We have recently reported that the use of an excess amount of DBU is essential for a catalytic reaction to proceed in the alkylative carboxylation of alkynes and zinc reagents by using a nickel(0) catalyst, see:, K. Shimizu, M. Takimoto, Y. Sato, M. Mori, Org. Lett. 2005, 7, 195.