Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: Total synthesis of erythrocarine

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2323-2325

  Shimizu, Kazuya ^a   Takimoto, Masanori ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ALKYNE DERIVATIVE; CARBON; ERYTHROCARINE; HETEROCYCLIC COMPOUND; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CATALYST; CYCLIZATION; SYNTHESIS;

ALKALOIDS; ALKYNES; ERYTHRINA; HETEROCYCLIC COMPOUNDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; NICKEL;

EID: 0141563504     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034670w     Document Type: Article

References (29)

1. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661. (b) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747. (c) Gibson, D. H. Chem. Rev. 1996, 96, 2063. (d) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
2. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661. (b) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747. (c) Gibson, D. H. Chem. Rev. 1996, 96, 2063. (d) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
3. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661. (b) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747. (c) Gibson, D. H. Chem. Rev. 1996, 96, 2063. (d) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
4. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661. (b) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747. (c) Gibson, D. H. Chem. Rev. 1996, 96, 2063. (d) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
5. (a) Hoberg, H.; Burkhart, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 76.
6. (b) Hoberg, H.; Schaefer, D. J. Organomet. Chem. 1982, 238, 383.
7. (c) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203.
8. (d) Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1999, 64, 3975.
9. Recent reports of catalytic reactions involving a related coupling process: (e) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. (f) Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saegusa, T. J. Org. Chem. 1990, 55, 2978. (g) Dèrien, S.; Clinet, J.-C.; Duñach, E.; Pèrichon, J. J. Am. Chem. Soc. 1991, 113, 8447. (h) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N.; J. Am. Chem. Soc. 2002, 124, 15189.
10. Recent reports of catalytic reactions involving a related coupling process: (e) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. (f) Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saegusa, T. J. Org. Chem. 1990, 55, 2978. (g) Dèrien, S.; Clinet, J.-C.; Duñach, E.; Pèrichon, J. J. Am. Chem. Soc. 1991, 113, 8447. (h) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N.; J. Am. Chem. Soc. 2002, 124, 15189.
11. Recent reports of catalytic reactions involving a related coupling process: (e) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. (f) Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saegusa, T. J. Org. Chem. 1990, 55, 2978. (g) Dèrien, S.; Clinet, J.-C.; Duñach, E.; Pèrichon, J. J. Am. Chem. Soc. 1991, 113, 8447. (h) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N.; J. Am. Chem. Soc. 2002, 124, 15189.
12. Recent reports of catalytic reactions involving a related coupling process: (e) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. (f) Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saegusa, T. J. Org. Chem. 1990, 55, 2978. (g) Dèrien, S.; Clinet, J.-C.; Duñach, E.; Pèrichon, J. J. Am. Chem. Soc. 1991, 113, 8447. (h) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N.; J. Am. Chem. Soc. 2002, 124, 15189.
13. (a) Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2001, 123, 2895.
14. (b) Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345.
15. (c) Takimoto, M. Mori, M. J. Am. Chem. Soc. 2002, 124, 10008.
16. Transmetalation of alkylzinc reagent to nickel, See: (a) Ikeda, S.; Kondo, K.; Sato, Y. Chem. Lett. 1999, 1227. (b) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (c) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. (d) Sato, Y.; Takanashi, T.; Mori, M. Organomet. 1999, 18, 4891.
17. Transmetalation of alkylzinc reagent to nickel, See: (a) Ikeda, S.; Kondo, K.; Sato, Y. Chem. Lett. 1999, 1227. (b) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (c) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. (d) Sato, Y.; Takanashi, T.; Mori, M. Organomet. 1999, 18, 4891.
18. Transmetalation of alkylzinc reagent to nickel, See: (a) Ikeda, S.; Kondo, K.; Sato, Y. Chem. Lett. 1999, 1227. (b) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (c) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. (d) Sato, Y.; Takanashi, T.; Mori, M. Organomet. 1999, 18, 4891.
19. Transmetalation of alkylzinc reagent to nickel, See: (a) Ikeda, S.; Kondo, K.; Sato, Y. Chem. Lett. 1999, 1227. (b) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (c) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. (d) Sato, Y.; Takanashi, T.; Mori, M. Organomet. 1999, 18, 4891.
20. (a) Hill, R. K. The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 281.
21. (b) Dyke, S. F.; Quessy, S. N. The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1981; Vol. 18, p 1.
22. Isolation of erythraline: (a) Folkers, K.; Koniuszy, F. J. Am. Chem. Soc. 1940, 62, 436. Total synthesis of erythraline: (b) Sano, T.; Toda, J.; Heterocycles 1982, 18, 229. (c) Sano, T.; Toda, J.; Kashiwaba, N.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Erythrocarine, isolation: (d) Chawla, A. S.; Redha, F. M. J.; Jackson, A. H. Phytochemistry 1985, 24, 1821.
23. Isolation of erythraline: (a) Folkers, K.; Koniuszy, F. J. Am. Chem. Soc. 1940, 62, 436. Total synthesis of erythraline: (b) Sano, T.; Toda, J.; Heterocycles 1982, 18, 229. (c) Sano, T.; Toda, J.; Kashiwaba, N.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Erythrocarine, isolation: (d) Chawla, A. S.; Redha, F. M. J.; Jackson, A. H. Phytochemistry 1985, 24, 1821.
24. Isolation of erythraline: (a) Folkers, K.; Koniuszy, F. J. Am. Chem. Soc. 1940, 62, 436. Total synthesis of erythraline: (b) Sano, T.; Toda, J.; Heterocycles 1982, 18, 229. (c) Sano, T.; Toda, J.; Kashiwaba, N.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Erythrocarine, isolation: (d) Chawla, A. S.; Redha, F. M. J.; Jackson, A. H. Phytochemistry 1985, 24, 1821.
25. Isolation of erythraline: (a) Folkers, K.; Koniuszy, F. J. Am. Chem. Soc. 1940, 62, 436. Total synthesis of erythraline: (b) Sano, T.; Toda, J.; Heterocycles 1982, 18, 229. (c) Sano, T.; Toda, J.; Kashiwaba, N.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Erythrocarine, isolation: (d) Chawla, A. S.; Redha, F. M. J.; Jackson, A. H. Phytochemistry 1985, 24, 1821.
26. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579.
27. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
28. Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801.
29. The protons of the lower field (the vinyl, aromatic ring and methylene dioxy protons) agree with those of erythrocarine reported in the literature, but those of higher field do not agree.