Total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A and their unnatural enantiomers: Assessment of chemical and biological properties

Journal of the American Chemical Society

Volumn 119, Issue 2, 1997, Pages 311-325

  Boger, Dale L ^a   McKie, Jeffrey A ^a   Nishi, Takahide ^a   Ogiku, Tsuyoshi ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DUOCARMYCIN A;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031055494     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962431g     Document Type: Article

References (97)

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53. Full experimental details and characterization are provided in the Supporting Information.
54. Mitsunobu, O. Synthesis 1981, 1.
55. Diagnostic characterization is provided in the Supporting Information.
56. Tsunoda, T.; Yamamiya, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639.
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62. The atomic coordinates have been deposited with the Cambridge X-ray Data Centre and may be obtained, on request, from the Director, Cambridge X-ray Data Centre, University Chemical Lab, Lensfield Road, Cambridge, CB2 1EW, UK.
63. For additional exceptions, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375. Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1994, 35, 425. Vanhessche, K.; Sharpless, K. B. Unpublished results. With optically active substrates and double diastereoselection: Carreira, E. M.; DuBois, J. J. Am. Chem. Soc. 1994, 116, 10825. Iwashima, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
64. For additional exceptions, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375. Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1994, 35, 425. Vanhessche, K.; Sharpless, K. B. Unpublished results. With optically active substrates and double diastereoselection: Carreira, E. M.; DuBois, J. J. Am. Chem. Soc. 1994, 116, 10825. Iwashima, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
65. For additional exceptions, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375. Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1994, 35, 425. Vanhessche, K.; Sharpless, K. B. Unpublished results. With optically active substrates and double diastereoselection: Carreira, E. M.; DuBois, J. J. Am. Chem. Soc. 1994, 116, 10825. Iwashima, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
66. For additional exceptions, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375. Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1994, 35, 425. Vanhessche, K.; Sharpless, K. B. Unpublished results. With optically active substrates and double diastereoselection: Carreira, E. M.; DuBois, J. J. Am. Chem. Soc. 1994, 116, 10825. Iwashima, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
67. For additional exceptions, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375. Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1994, 35, 425. Vanhessche, K.; Sharpless, K. B. Unpublished results. With optically active substrates and double diastereoselection: Carreira, E. M.; DuBois, J. J. Am. Chem. Soc. 1994, 116, 10825. Iwashima, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
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97. Characterization for the diastereomeric series 45-50 and 68-70 is provided in the Supporting Information.