Oxidative intramolecular [4 + 2]cycloaddition of silylene-protected 2-pyridone derivatives—a short and efficient synthesis of the DEF-ring of fredericamycin A

Yasuyuki Kita; Hiroshi Ueno; Shinji Kitagaki; Kyoko Kobayashi; Kiyosei Lio; Shuji Akai

doi:10.1039/C39940000701

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Oxidative intramolecular [4 + 2]cycloaddition of silylene-protected 2-pyridone derivatives—a short and efficient synthesis of the DEF-ring of fredericamycin A

Yasuyuki Kita, Hiroshi Ueno, Shinji Kitagaki, Kyoko Kobayashi, Kiyosei Lio and Shuji Akai

Abstract

Thermal treatment of 2-pyridone derivatives 2 with dimethyldichlorosilane, triethylamine and chloranil in benzene gives 8-hydroxyisoquinolones 4 in high yields by oxidative intramolecular [4 + 2]cycloaddition which are used in the synthesis of the fully functionalized DEF-ring 14 of fredericamycin A.

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DOI: https://doi.org/10.1039/C39940000701
Article type: Paper

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J. Chem. Soc., Chem. Commun., 1994, 701-702

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Oxidative intramolecular [4 + 2]cycloaddition of silylene-protected 2-pyridone derivatives—a short and efficient synthesis of the DEF-ring of fredericamycin A

Y. Kita, H. Ueno, S. Kitagaki, K. Kobayashi, K. Lio and S. Akai, J. Chem. Soc., Chem. Commun., 1994, 701 DOI: 10.1039/C39940000701

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Journal of the Chemical Society, Chemical Communications

Oxidative intramolecular [4 + 2]cycloaddition of silylene-protected 2-pyridone derivatives—a short and efficient synthesis of the DEF-ring of fredericamycin A

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Oxidative intramolecular [4 + 2]cycloaddition of silylene-protected 2-pyridone derivatives—a short and efficient synthesis of the DEF-ring of fredericamycin A

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