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Volumn 122, Issue 4, 2000, Pages 571-575

A powerful o-quinone dimethide strategy for intermolecular Diels-Alder cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; IDARUBICIN; IDARUBICIN DERIVATIVE; NAPHTHALENE DERIVATIVE; QUINONE DERIVATIVE;

EID: 0033952620     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993627u     Document Type: Article
Times cited : (56)

References (73)
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    • trans-Diacyloxy-substituted benzocyclobutenes of type 3 give Diels-Alder products with 42 at 80°C. Elaboration into the naphthoquinone was not possible, and in practice, thermal elimination of the diacetoxy groups gave the corresponding anthracene: (a) Hassall, C. H.; Broadhurst, M. J.; Thomas, G. J. J. Chem. Soc., Perkin Trans. 1 1982, 2239. (b) Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. Tetrahedron 1984, 40, 4649.
    • (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2239
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    • trans-Diacyloxy-substituted benzocyclobutenes of type 3 give Diels-Alder products with 42 at 80°C. Elaboration into the naphthoquinone was not possible, and in practice, thermal elimination of the diacetoxy groups gave the corresponding anthracene: (a) Hassall, C. H.; Broadhurst, M. J.; Thomas, G. J. J. Chem. Soc., Perkin Trans. 1 1982, 2239. (b) Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. Tetrahedron 1984, 40, 4649.
    • (1984) Tetrahedron , vol.40 , pp. 4649
    • Broadhurst, M.J.1    Hassall, C.H.2    Thomas, G.J.3
  • 54
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    • Silyloxy-substituted benzocyclobutenes have also been prepared by Suzuki: (e) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377. (f) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177. (g) Matsumoto, T.; Hamura, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1997, 38, 8985.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3377
    • Hosoya, T.1    Hasegawa, T.2    Kuriyama, Y.3    Suzuki, K.4
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    • Silyloxy-substituted benzocyclobutenes have also been prepared by Suzuki: (e) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377. (f) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177. (g) Matsumoto, T.; Hamura, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1997, 38, 8985.
    • (1995) Synlett , pp. 177
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  • 56
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    • Silyloxy-substituted benzocyclobutenes have also been prepared by Suzuki: (e) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377. (f) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177. (g) Matsumoto, T.; Hamura, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1997, 38, 8985.
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  • 57
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    • note
    • Bis(trimethylsilyloxy) derivatives 11 and 33 were obtained in 4:1-6:1 trans/cis ratios. The bis(tert-butyldimethylsilyloxy) derivatives 12 and 27 were obtained in 6:1-9:1 trans/cis ratios. The difference was possibly due to partial decompostion of the trans isomer during preparation of 11 and 33.
  • 61
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    • note
    • Relative configuration of the adducts were determined by 2-D and NOE NMR experiments. All product ratios were determined by integration in the NMR spectra.
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    • 4: (a) Jung, M. E. J. Org. Chem. 1976, 41, 1479. See also: (b) Muzart, J. Synthesis 1993, 11.
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  • 67
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    • note
    • Compound 28 was obtained as a 4:3 mixture of endo and exo diastereomers.
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    • Idarubicin (Idamycin) was approved in 1990 for use in the United States for treatment of acute nonlymphocytic and lymphoblastic leukemia. It has been shown to have superior therapeutic efficacy and reduced cardiotoxicity and to provide longer duration of survival compared to Daunorubicin: (a) Hollingshead, L. M.; Faulds, D. Drugs 1991, 42, 690. (b) Cersosimo, R. J. Clin. Pharm. 1992, 11, 152. Idarubicin is produced, with some difficulty, by semisynthesis from Daunomycin: Penco, S. Chim. Ind. Milan 1993, 75, 369; EP 0 337 665 B1.
    • (1991) Drugs , vol.42 , pp. 690
    • Hollingshead, L.M.1    Faulds, D.2
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    • Idarubicin (Idamycin) was approved in 1990 for use in the United States for treatment of acute nonlymphocytic and lymphoblastic leukemia. It has been shown to have superior therapeutic efficacy and reduced cardiotoxicity and to provide longer duration of survival compared to Daunorubicin: (a) Hollingshead, L. M.; Faulds, D. Drugs 1991, 42, 690. (b) Cersosimo, R. J. Clin. Pharm. 1992, 11, 152. Idarubicin is produced, with some difficulty, by semisynthesis from Daunomycin: Penco, S. Chim. Ind. Milan 1993, 75, 369; EP 0 337 665 B1.
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    • Idarubicin (Idamycin) was approved in 1990 for use in the United States for treatment of acute nonlymphocytic and lymphoblastic leukemia. It has been shown to have superior therapeutic efficacy and reduced cardiotoxicity and to provide longer duration of survival compared to Daunorubicin: (a) Hollingshead, L. M.; Faulds, D. Drugs 1991, 42, 690. (b) Cersosimo, R. J. Clin. Pharm. 1992, 11, 152. Idarubicin is produced, with some difficulty, by semisynthesis from Daunomycin: Penco, S. Chim. Ind. Milan 1993, 75, 369; EP 0 337 665 B1.
    • (1993) Ind. Milan , vol.75 , pp. 369
    • Chim, P.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.