The first total synthesis of dragmacidin D

Journal of the American Chemical Society

Volumn 124, Issue 44, 2002, Pages 13179-13184

  Garg, Neil K ^a   Sarpong, Richmond ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS;

CATALYSIS; MODULATION; PALLADIUM; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

DRUG PRODUCTS;

ALKALOID; DRAGMACIDIN; DRAGMACIDIN A; DRAGMACIDIN B; DRAGMACIDIN C; DRAGMACIDIN D; DRAGMACIDIN E; DRAGMACIDIN F; GUANIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; THERMAL ANALYSIS;

ANIMALS; ENZYME INHIBITORS; INDOLE ALKALOIDS; INDOLES; PIPERAZINES; PORIFERA;

EID: 0037032310     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027822b     Document Type: Article

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23. Although some elegant synthetic work directed at the piperazine-containing dragmacidins has appeared, reports directed toward those members possessing guanidine-functionalized indoles around a pyrazinone core have been limited. For synthetic work aimed at the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett, 2002, 43, 4245-4248. For studies specifically targeting dragmacidins D, E, or F, see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371. (h) Jiang, B.: Gu, X.-H. Heterocycles 2000, 53, 1559-1568. (i) Yakushijin, K.; Horne, D. A. PCT Int. Appl. WO 0194310 A1, December 13, 2001. (j) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066. (k) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
24. Although some elegant synthetic work directed at the piperazine-containing dragmacidins has appeared, reports directed toward those members possessing guanidine-functionalized indoles around a pyrazinone core have been limited. For synthetic work aimed at the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett, 2002, 43, 4245-4248. For studies specifically targeting dragmacidins D, E, or F, see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371. (h) Jiang, B.: Gu, X.-H. Heterocycles 2000, 53, 1559-1568. (i) Yakushijin, K.; Horne, D. A. PCT Int. Appl. WO 0194310 A1, December 13, 2001. (j) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066. (k) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
25. Although some elegant synthetic work directed at the piperazine-containing dragmacidins has appeared, reports directed toward those members possessing guanidine-functionalized indoles around a pyrazinone core have been limited. For synthetic work aimed at the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett, 2002, 43, 4245-4248. For studies specifically targeting dragmacidins D, E, or F, see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371. (h) Jiang, B.: Gu, X.-H. Heterocycles 2000, 53, 1559-1568. (i) Yakushijin, K.; Horne, D. A. PCT Int. Appl. WO 0194310 A1, December 13, 2001. (j) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066. (k) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
26. Although some elegant synthetic work directed at the piperazine-containing dragmacidins has appeared, reports directed toward those members possessing guanidine-functionalized indoles around a pyrazinone core have been limited. For synthetic work aimed at the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett, 2002, 43, 4245-4248. For studies specifically targeting dragmacidins D, E, or F, see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371. (h) Jiang, B.: Gu, X.-H. Heterocycles 2000, 53, 1559-1568. (i) Yakushijin, K.; Horne, D. A. PCT Int. Appl. WO 0194310 A1, December 13, 2001. (j) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066. (k) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
27. Although some elegant synthetic work directed at the piperazine-containing dragmacidins has appeared, reports directed toward those members possessing guanidine-functionalized indoles around a pyrazinone core have been limited. For synthetic work aimed at the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett, 2002, 43, 4245-4248. For studies specifically targeting dragmacidins D, E, or F, see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371. (h) Jiang, B.: Gu, X.-H. Heterocycles 2000, 53, 1559-1568. (i) Yakushijin, K.; Horne, D. A. PCT Int. Appl. WO 0194310 A1, December 13, 2001. (j) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066. (k) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
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