Absolute configuration and total synthesis of (+)-curacin A, an antiproliferative agent from the cyanobacterium Lyngbya majuscula

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 103-111

  White, James D ^a   Kim, Tae Seong ^a   Nambu, Mitch ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CURACIN A;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CYANOBACTERIUM; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 0031055522     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9629874     Document Type: Article

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28. Preliminary account: White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995,117, 5612. Subsequent to this report, syntheses of curacin A have been described by Aubé (Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953), by Kobayashi (Ito, H.; Imai, N.; Takao, K.-I.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799), by Iwasaki (Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397), by Wipf (Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556), and by Falck (Lai, J.-Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167).
29. Preliminary account: White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995,117, 5612. Subsequent to this report, syntheses of curacin A have been described by Aubé (Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953), by Kobayashi (Ito, H.; Imai, N.; Takao, K.-I.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799), by Iwasaki (Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397), by Wipf (Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556), and by Falck (Lai, J.-Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167).
30. Preliminary account: White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995,117, 5612. Subsequent to this report, syntheses of curacin A have been described by Aubé (Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953), by Kobayashi (Ito, H.; Imai, N.; Takao, K.-I.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799), by Iwasaki (Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397), by Wipf (Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556), and by Falck (Lai, J.-Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167).
31. Preliminary account: White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995,117, 5612. Subsequent to this report, syntheses of curacin A have been described by Aubé (Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953), by Kobayashi (Ito, H.; Imai, N.; Takao, K.-I.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799), by Iwasaki (Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397), by Wipf (Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556), and by Falck (Lai, J.-Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167).
32. Preliminary account: White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995,117, 5612. Subsequent to this report, syntheses of curacin A have been described by Aubé (Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953), by Kobayashi (Ito, H.; Imai, N.; Takao, K.-I.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799), by Iwasaki (Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397), by Wipf (Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556), and by Falck (Lai, J.-Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167).
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47. 3 solution, resulting in decreasing optical rotation with time in this solvent.