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Issue 0, 1982
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New stereoselective synthesis of 9-methyl-cis-decalin derivatives by double Michael reaction of 3-methyl-4-methylenecyclohex-2-enone and its congeners with dimethyl 3-oxoglutarate

Hiroshi Irie,  Yukio Mizuno,  Tooru Taga  and  Kenji Osaki 

Abstract

Double Michael reaction of 3-methyl-, 2,3-dimethyl-, and 3,5-dimethyl-4-methylenecyclohex-2-enone with dimethyl 3-oxoglutarate in dimethyl sulphoxide in the presence of potassium fluoride gave stereoselectively 9-methyl-, 1,9-dimethyl-, and 4,9-dimethyl-6,8-dimethoxycarbonyl-cis-decahydronaphthalene-2,7-dione, respectively, and starting from these annulation products some sesquiterpenes having the cis-decahydronaphthalene skeleton were formally synthesised.

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Article type: Paper
DOI: 10.1039/P19820000025
Citation: J. Chem. Soc., Perkin Trans. 1, 1982,0, 25-30
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    New stereoselective synthesis of 9-methyl-cis-decalin derivatives by double Michael reaction of 3-methyl-4-methylenecyclohex-2-enone and its congeners with dimethyl 3-oxoglutarate

    H. Irie, Y. Mizuno, T. Taga and K. Osaki, J. Chem. Soc., Perkin Trans. 1, 1982, 0, 25
    DOI: 10.1039/P19820000025

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