- Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
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Described is the development of a highly efficient 2πdisrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester. Cracked open: A highly efficient thermal 2πdisrotatory ring-opening aromatization sequence of bicyclo[3.1.0]hexan-2-ones is described. The transformation proceeds in sulfolane to give uniquely substituted benzoates. In the presence of either amines or alcohols, formation of substituted anilines or ethers, respectively, is achieved.
- Feierfeil, Johannes,Grossmann, Adriana,Magauer, Thomas
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p. 11835 - 11838
(2015/10/05)
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- Synthetic Microbial Chemistry, XXI. Synthesis of Differanisole A, an Inducer of Differentiation
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The synthesis of differanisole A (3,5-dichloro-2-hydroxy-4-methoxy-6-propylbenzoic acid, 1) was achieved in five steps from 2-pentanone.
- Mori, Kenji,Kamada, Atsushi,Mori, Hideto
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p. 303 - 306
(2007/10/02)
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- Thermal Decomposition of Lichen Depsides
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The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition
- Huneck, Siegfried,Schmidt, Juergen,Tabacchi, Raffaele
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p. 1283 - 1289
(2007/10/02)
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