Photooxidative dehydrogenation of Δ8-drimen-and Δ8-11-homodrimen-7-ones into α,α ′-dienones |
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| Authors: | P F Vlad M N Coltsa A N Aricu A G Ciocarlan E C Gorincioi C G Edu C Deleanu |
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| Institution: | (1) Institute of Chemistry, Academy of Sciences of the Republic of Moldova, 3 ul. Academiei, MD-2028 Chisinau, Republic of Moldova;(2) Institute of Organic Chemistry of the Romanian Academy of Sciences, ul. Independentei, 202B, RO-71141 Bucharest, Romania |
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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.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 678–682, April, 2006. |
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| Keywords: | photosensitized oxygenation photooxidative dehydrogenation drim-8-en-7-ones drima-5 8-dien-7-ones methyl 7-oxo-11-homodrim-8-en-12-oate methyl 7-oxo-11-homodrim-5 8-dien-12-oate |
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