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Synthesis of the bicyclo[6.2.1]undecane ring system by a solvent-free Diels–Alder reaction |
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| Authors: | Adilson Beatriz Roberto da Silva Gomes Mauricio Gomes Constantino Gil Valdo José da Silva Kleber Thiago de Oliveira |
| Institution: | 1. Instituto de Química, Universidade Federal de Mato Grosso do Sul, Avenida Senador Filinto Muller, 1555, Cidade Universitária, 79074-460 Campo Grande, MS, Brazil;2. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, 14040-901 Ribeirão Preto, SP, Brazil;3. Departamento de Química, Centro de Ciências Exatas e Tecnologia, Universidade Federal de São Carlos, Rodovia Washington Luis, Km 235, Monjolinho, 13565-905 São Carlos, SP, Brazil |
| Abstract: | A bicyclo6.2.1]undecane model compound of the core structure of the biologically active furanoheliangolide sesquiterpene was synthesized. This new and short route was developed by using a solvent-free Diels–Alder reaction between cyclopentadiene and 3-nitro-2-cyclohexenone, followed by simple transformations. Theoretical calculations were performed in order to understand reactivity aspects of the cycloaddition. |
| Keywords: | Furanoheliangolide Sesquiterpene Diels&ndash Alder Solvent-free DFT calculations |
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