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Volumn 46, Issue 3, 1998, Pages 400-412

Synthesis of duocarmycin SA by way of methyl 4-(Methoxycarbonyl)oxy-3H- pyrrolo[3,2-f]quinoline-2-carboxylate as a tricyclic heteroaromatic intermediate

Author keywords

Duocarmycin SA; Formal synthesis; Methyl ketone arylation; Palladium catalyzed reaction; Potent antitumor substance; Stille reaction

Indexed keywords

4 (METHOXYCARBONYL)OXY 3H PYRROLO[3,2]QUINOLINE 2 CARBOXYLIC ACID METHYL ESTER; CARBOXYLIC ACID DERIVATIVE; DUOCARMYCIN A; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

EID: 0031978519     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.400     Document Type: Article
Times cited : (24)

References (48)
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    • Isolation and Structure Determination: a) Ichimura M., Ogawa T., Takahashi K., Kobayashi E., Kawamoto I., Yasuzawa T., Takahashi I., Nakano H., J. Antibiot., 43, 1037-1038 (1990); b) Yasuzawa T., Saitoh Y., Ichimura M., Takahashi I., Sano H., ibid., 44, 445-447 (1991); c) Ichimura M., Ogawa T., Katsumata S., Takahashi K., Takahashi I., Nakano H., ibid., 44, 1045-1053 (1991).
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    • Isolation and Structure Determination: a) Ichimura M., Ogawa T., Takahashi K., Kobayashi E., Kawamoto I., Yasuzawa T., Takahashi I., Nakano H., J. Antibiot., 43, 1037-1038 (1990); b) Yasuzawa T., Saitoh Y., Ichimura M., Takahashi I., Sano H., ibid., 44, 445-447 (1991); c) Ichimura M., Ogawa T., Katsumata S., Takahashi K., Takahashi I., Nakano H., ibid., 44, 1045-1053 (1991).
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    • Other Syntheses: a) Boger D. L., Machiya K., J. Am. Chem. Soc., 114, 10056-10058 (1992); b) Boger D. L., Machiya K., Hertzog D. L., Kilos P. A., Holmes D., ibid., 115, 9025-9036 (1993); c) Muratake H., Matsumura N., Natsume M., Chem. Pharm. Bull., 43, 1064-1066 (1995).
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    • Other Syntheses: a) Boger D. L., Machiya K., J. Am. Chem. Soc., 114, 10056-10058 (1992); b) Boger D. L., Machiya K., Hertzog D. L., Kilos P. A., Holmes D., ibid., 115, 9025-9036 (1993); c) Muratake H., Matsumura N., Natsume M., Chem. Pharm. Bull., 43, 1064-1066 (1995).
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    • Other Syntheses: a) Boger D. L., Machiya K., J. Am. Chem. Soc., 114, 10056-10058 (1992); b) Boger D. L., Machiya K., Hertzog D. L., Kilos P. A., Holmes D., ibid., 115, 9025-9036 (1993); c) Muratake H., Matsumura N., Natsume M., Chem. Pharm. Bull., 43, 1064-1066 (1995).
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    • Reviews: a) Boger D. L., Acc. Chem. Res., 28, 20-29 (1995); b) Boger D. L., Johnson D. S., Angew. Chem. Int., Ed. Engl., 35, 1438-1474 (1996); c) Boger D. L., Boyce, C. W., Garbaccio R. M., Goldberg, J. A., Chem. Rev., 97, 787-828 (1997).
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    • Reviews: a) Boger D. L., Acc. Chem. Res., 28, 20-29 (1995); b) Boger D. L., Johnson D. S., Angew. Chem. Int., Ed. Engl., 35, 1438-1474 (1996); c) Boger D. L., Boyce, C. W., Garbaccio R. M., Goldberg, J. A., Chem. Rev., 97, 787-828 (1997).
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    • Reviews: a) Stille J. K., Angew. Chem., 98, 504-519 (1986); Angew. Chem., Int. Ed. Engl. 25, 508-524 (1986); b) Mitchell T. N., Synthesis, 1992, 803-815; c) Ritter K., ibid., 1993, 735-762.
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    • note
    • Reaction of nitromethane with 1-methoxypyridinium iodide in the presence of sodium methoxide in ethanol at room temperature gave l-methoxyimino-6-aci-nitrohexa-2,4-dienc in 60% yield. Okamoto T., Takayama H., private communication, 1961.
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    • b) Crispino G. A., Jeong K.-S., Kolb H. C., Wang Z.-M., Xu D., Sharpless K. B., ibid., 58, 3785-3786 (1993). Review: Kolb H. C., VanNieuwenhze M. S., Sharpless K. B., Chem. Rev., 94, 2483-2547 (1994).
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  • 47
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    • Boger and co-workers reported a similar Jacobsen epoxidation of a benzene analog related to our dihydropyridine derivative, which gave an optically active epoxide of 92% ee in 70% yield. Boger D. L., McKie J. A., Boyce C. W., Synlett, 1997, 515-517.
    • Synlett , vol.1997 , pp. 515-517
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