A novel phenol-forming reaction for preparation of benzene, furan, and thiophene analogs of CC-1065/duocarmycin pharmacophores

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7577-7580

  Muratake, Hideaki ^a   Hayakawa, Aki ^a   Natsume, Mitsutaka ^a  

^a Kawasaki   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; RACHELMYCIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030808981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01786-3     Document Type: Article

References (22)

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3. b) Boger, D.L.; Johnson, D.S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1438-1474.
4. c) Boger, D.L.; Boyce, C.W.; Garbaccio, R.M.; Goldberg, J.A. Chem. Rev. 1997, 97, 787-828.
5. Total syntheses: a) Boger, D.L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056-10058.
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10. f) Reference 1.
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12. b) Yasuzawa, T.; Saitoh, Y.; Ichimura, M.; Takahashi, I.; Sano, H. J. Antibiot. 1991, 44, 445-447.
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15. According to the description in the ref. 1, 10, 11, and 12 were prepared as follows: Stille couplings between either of 2-bromoacetophenone, 2-acetyl-3-bromofuran, or 2-acetyl-3-bromothiophene and 3 afforded in 67%, 80%, and 74% yields the condensation products, which were hydrolyzed to pyridones in 97%, 90%, and 93% yields. These were triflated to 10, 11, and 12 in 96%, 98%, and 98% yields.
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22. This work was supported by a Grant-in-Aid from the Ministry of Education, Science, Sports and Culture, which is acknowledged.