Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2227-2230

  Boger, Dale L ^a   Boyce, Christopher W ^a   Garbaccio, Robert M ^a   Searcey, Mark ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DUOCARMYCIN A; RACHELMYCIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DNA ALKYLATION; DRUG CONFORMATION; DRUG DNA INTERACTION; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0032537208     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00232-9     Document Type: Article

References (22)

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5. 5. For a review of mechanistic aspects see: Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1438.
6. 6. For a review of synthetic efforts see: Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
7. 7. Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mésini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987. Boger, D. L.; Garbaccio, R. M. Bioorg. Med. Chem. 1997, 5, 263.
8. 7. Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mésini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987. Boger, D. L.; Garbaccio, R. M. Bioorg. Med. Chem. 1997, 5, 263.
9. 7. Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mésini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987. Boger, D. L.; Garbaccio, R. M. Bioorg. Med. Chem. 1997, 5, 263.
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16. 11. For a review of the evolution of a free radical cyclization approach to CC-1065/duocarmycins and their analogs, see: Boger, D. L. Israel J. Chem. 1997, 37, 119.
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18. 13. TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; AIBN = 2,2'-azobisisobutyronitrile
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22. 2, 2.5 × 15 cm, 10% EtOAc/hexane) gave a further 81 mg of 12a, providing a total yield of 381 mg (90%).