Total synthesis of merrilactone A

Journal of the American Chemical Society

Volumn 125, Issue 36, 2003, Pages 10772-10773

  Inoue, Masayuki ^a   Sato, Takaaki ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; MERRILACTONE A; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ILLICIUM; LACTONES; SESQUITERPENES;

EID: 0043236240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036587+     Document Type: Article

References (46)

1. (a) Huang, J.-M.; Yokoyama, R.; Yang C.-S.; Fukuyama, Y. Tetrahedron Lett. 2000, 41, 6111.
2. (b) Huang, J.-M.; Yang, C.-S.; Tanaka, M.; Fukuyama, Y. Tetrahedron 2001, 57, 4691.
3. For a review on neurotrophic activity, see: Hefti, F. Annu. Rev. Pharmacol. Toxicol. 1997, 37, 239.
4. Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080.
5. For a synthetic study, see: Hong, B.-C.; Shr, Y.-J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249.
6. For reviews on the construction of eight-membered rings, see: (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757. (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
7. For reviews on the construction of eight-membered rings, see: (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757. (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
8. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
9. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
10. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
11. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
12. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
13. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
14. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
15. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
16. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
17. For selected examples of the synthesis of bicyclo[3.3.0]octane systems from eight-membered rings, see: (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189. (b) Paquette, L. A.; Geng, F. J. Am. Chem. Soc. 2002, 124, 9199. For a review of extensive studies in this field by Paquette, see: (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. (d) Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523. (e) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (f) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111. (g) Verma, S. K.; Fleischer, E. B.; Moore, H. W. J. Org. Chem. 2000, 65, 8564. (h) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. (i) Dongol, K. G.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 2002, 1972. (j) Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
18. For reviews on the related approaches including two-directional synthesis, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9. (b) Magnuson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. 2003, 42, 1096.
19. For reviews on the related approaches including two-directional synthesis, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9. (b) Magnuson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. 2003, 42, 1096.
20. For reviews on the related approaches including two-directional synthesis, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9. (b) Magnuson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. 2003, 42, 1096.
21. (a) Schenck, G. O.; Hartmann, W.; Steinmetz, R. Chem. Ber. 1963, 96, 498.
22. (b) Gauvry, N.; Comoy, C.; Lescop, C.; Huet, F. Synthesis 1999, 574.
23. Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198.
24. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. For recent reviews of RCM, see: (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
25. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. For recent reviews of RCM, see: (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
26. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. For recent reviews of RCM, see: (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
27. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. For recent reviews of RCM, see: (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
28. Balskus, E. P.; Méndez-Andino, J.; Arbit, R. M.; Paquette, L. A. J. Org. Chem. 2001, 66, 6695.
29. Zhao, P.; Collum, D. B. J. Am. Chem. Soc. 2003, 125, 4008.
30. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
31. (b) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
32. (a) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547. For a review, see: (b) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415.
33. (a) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547. For a review, see: (b) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415.
34. (a) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. For a recent review on radical reactions, see: (c) Zhang, W. Tetrahedron 2001, 57, 7237.
35. (a) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. For a recent review on radical reactions, see: (c) Zhang, W. Tetrahedron 2001, 57, 7237.
36. (a) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. For a recent review on radical reactions, see: (c) Zhang, W. Tetrahedron 2001, 57, 7237.
37. Danishefsky, S.; Kitahara, T.; McKee, R.; Schuda, P. F. J. Am. Chem. Soc. 1976, 98, 6715.
38. The reductions of many other substrates led to low chemo- or stereoselectivity, which will be discussed in a full account.
39. Crisp, G. T.; Scott, W. J. Synthesis 1985, 335.
40. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33. 6299.
41. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
42. (a) Fetizon, M.; Golfier, M. Compt. Rend. 1968, 267, 900.
43. (b) McKillop, A.; Young, D. W. Synthesis 1979, 401.
44. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187.
45. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
46. Professor Y. Fukuyama (Tokushima Bunri University) is gratefully acknowledged for providing NMR spectra of merrilactone A.