Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agents

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 11953-11963

  Depew, Kristopher M ^a,b,c   Marsden, Stephen P ^a,d   Zatorska, Danuta ^a   Zatorski, Andrzej ^a   Bornmann, William G ^a   Danishefsky, Samuel J ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c HARVARD UNIVERSITY   (United States)

^d IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 N ACETYLARDEEMIN; ALKALOID DERIVATIVE; AMAUROMINE; DOXORUBICIN; PACLITAXEL; UNCLASSIFIED DRUG; VINBLASTINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYTOTOXICITY; DRUG SYNTHESIS; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; OXIDATION; STEREOCHEMISTRY;

EID: 0033616097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991558d     Document Type: Article

References (73)

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56. 2-symmetry. This product potentially represents a very direct solution to the problem of constructing fungal natural products of the C3a-bis(pyrroloindole) alkaloid class such as (a) the leptosins: Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Tanaka, H. Phytochemistry 1995, 38, 155. (b) Chaetocin: Weber, H. P. Acta Crystallogr. B 1972, 28, 2945. (c) Ditryptophenaline: Springer, J. P.; Buchi, G.; Clardy, J. Tetrahedron Lett. 1977, 18, 2403. (d) WIN 64821: Barrow, C. J.; Cai, P.; Snyder, J. K.; Sedlock, D. M.; Sun, H. H.; Cooper, R. J. Org. Chem. 1993, 58, 6016. See Supporting Information for details.
57. 2-symmetry. This product potentially represents a very direct solution to the problem of constructing fungal natural products of the C3a-bis(pyrroloindole) alkaloid class such as (a) the leptosins: Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Tanaka, H. Phytochemistry 1995, 38, 155. (b) Chaetocin: Weber, H. P. Acta Crystallogr. B 1972, 28, 2945. (c) Ditryptophenaline: Springer, J. P.; Buchi, G.; Clardy, J. Tetrahedron Lett. 1977, 18, 2403. (d) WIN 64821: Barrow, C. J.; Cai, P.; Snyder, J. K.; Sedlock, D. M.; Sun, H. H.; Cooper, R. J. Org. Chem. 1993, 58, 6016. See Supporting Information for details.
58. 2-symmetry. This product potentially represents a very direct solution to the problem of constructing fungal natural products of the C3a-bis(pyrroloindole) alkaloid class such as (a) the leptosins: Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Tanaka, H. Phytochemistry 1995, 38, 155. (b) Chaetocin: Weber, H. P. Acta Crystallogr. B 1972, 28, 2945. (c) Ditryptophenaline: Springer, J. P.; Buchi, G.; Clardy, J. Tetrahedron Lett. 1977, 18, 2403. (d) WIN 64821: Barrow, C. J.; Cai, P.; Snyder, J. K.; Sedlock, D. M.; Sun, H. H.; Cooper, R. J. Org. Chem. 1993, 58, 6016. See Supporting Information for details.
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65. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
66. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
67. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
68. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
69. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
70. For some additional studies in the ardeemin area see: (a) Martin- Santamaria, S.; Espada, M.; Avendano, C. Tetrahedron 1997, 53, 16795. (b) Bartolome, M. T.; Buenadicha, F. L.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 249. (c) Buenadicha, F. L.; Bartolome, M. T.; Aguirre, M. J.; Avendaño, C.; Sollhuber, M. Tetrahedron-Asym. 1998, 9, 483. (d) Madrigal, A.; Grande, M.; Avendaño, C. J. Org. Chem. 1998, 63, 2724. (e) Fernandez, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777. (f) Sanchez, J. D.; Ramos, M. T.; Avendaño, C. Tetrahedron 1998, 54, 969. (g) Caballero, E.; Avendano, C.; Menendez, J. C. Tetrahedron Asymmetry 1998, 9, 3025.
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