Epimerization of 6-Protoilluden-8-one at C-3 and the Relative Thermodynamic Stabilities of Stereoisomeric 6-Protoilluden-8-ones

NAOKO MORISAKI; JUN FURUKAWA; HISAYOSHI KOBAYASHI; SHIGEO IWASAKI; AKIKO ITAI; SHIGEO NOZOE; SHIGENOBU OKUDA

doi:10.1248/cpb.33.2792

NAOKO MORISAKI, JUN FURUKAWA, HISAYOSHI KOBAYASHI, SHIGEO IWASAKI, AKIKO ITAI, SHIGEO NOZOE, SHIGENOBU OKUDA

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Keywords: cyclobutyl-cyclopropylcarbinyl cation rearrangement

JOURNAL FREE ACCESS

1985 Volume 33 Issue 7 Pages 2792-2797

DOI https://doi.org/10.1248/cpb.33.2792

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Abstract

Both 9-epi-6-protoilluden-8-one (5) and 6-protoilluden-8-one (4) underwent cyclobutylcyclopropylcarbinyl cation rearrangement on treatment with CF₃COOH (25%)-CHCl₃, to give 2, 9-cis-2, 3-syn 6-protoilluden-8-one (6). In order to elucidate the relative thermodynamic stabilities of these stereoisomeric enones (4-7), molecular mechanical calculations were carried out. The result showed that the cis-syn enone 6 is the most stable one. This is in good agreement with the experimental results.

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