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Photooxidative dehydrogenation of Δ8-drimen-and Δ8-11-homodrimen-7-ones into α,α ′-dienones

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Abstract

An efficient two-step procedure for photooxidative dehydrogenation of drimane and 11-homodrimane compounds containing an 8-en-7-one structural unit into α,α′-dienones was elaborated. The method is based on the transformation of ketones into the respective enol acetates followed by photosensitized oxygenation. Methyl 7-oxo-11-homodrima-5,8-dien-12-oate, 5,6-dehydro-7-ketoisodrimenine, 11-acetoxydrima-5,8-dien-7-one and 11,12-diacetoxydrima-5,8-dien-7-one were prepared in high yields starting from methyl 7-oxo-11-homodrim-8-en-12-oate, 7-oxoisodrimenine, 11-hydroxydrim-8-en-7-one and 11,12-diacetoxydrim-8-en-7-one, respectively.

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of the Republic of Moldova, 3 ul. Academiei, MD-2028, Chisinau, Republic of Moldova

    P. F. Vlad, M. N. Coltsa, A. N. Aricu, A. G. Ciocarlan, E. C. Gorincioi & C. G. Edu

  2. Institute of Organic Chemistry of the Romanian Academy of Sciences, ul. Independentei, 202B, RO-71141, Bucharest, Romania

    C. Deleanu

Authors
  1. P. F. Vlad
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  2. M. N. Coltsa
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  3. A. N. Aricu
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  4. A. G. Ciocarlan
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  5. E. C. Gorincioi
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  6. C. G. Edu
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  7. C. Deleanu
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Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 678–682, April, 2006.

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Vlad, P.F., Coltsa, M.N., Aricu, A.N. et al. Photooxidative dehydrogenation of Δ8-drimen-and Δ8-11-homodrimen-7-ones into α,α ′-dienones. Russ Chem Bull 55, 703–707 (2006). https://doi.org/10.1007/s11172-006-0316-x

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  • DOI: https://doi.org/10.1007/s11172-006-0316-x

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