Studies on Synthesis of 10,11-Dihydro-5H-dibenzo[a, d]cycloheptene Derivatives, III. : Stereostructures of Isomeric 8,9-Dimethoxycarbonyldibenzo[2,3 : 5,6]bicyclo[5.2.0]nonan-4-ones Determined by ^1H-^1H and ^<13>C-{^1H}Nuclear Overhauser Effects in Nucle
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Stereochemistry of 8,9-dimethoxycarbonyldibenzo[2,3 : 5,6]bycyclo[5.2.0]nonan-4-ones (2a, 3a, 4a, and 5a) and 8,9-dimethoxycarbonyl-4-hydroxydibenzo[2,3 : 5,6]tricyclo[5.2.0.0^<4.8>]nonanes (6a and 7a) was studied by chemical and spectrometrical means.Intramolecular acid anhydride formation reactions of isomeric cis-dicarboxylic acids (3c, 5c, 6c, and 4c) afforded the anhydrides (3d, 5d, 6d, and 5d), respectively. Interconversion between 2a and 3a and between 4a and 5a at higher temperature by thermal reaction resulted in equilibria of 2a and 3a (3 : 2) and of 4a and 5a (20 : 1).Detailed ^<13>C and ^1H assignments (3a, 4a, 5a, 6a, and 7a), and stereostructural assignments (3a, 4a, and 5a) were made by using nuclear magnetic resonance (NMR) techniques such as ^1H-{^1H} and ^<13>C-{^1H}NMR, ^<13>C/^1H chemical shift-correlated NMR, and ^1H-^1H and <13>C-{^1H} nuclear Overhauser effect (NOE) measurements. Moreover, a possible mechanism of interconversion between 4a and 5a is discussed.
- 公益社団法人日本薬学会の論文
- 1989-02-25
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