Synthesis of natural phenylpropanoid esters via conventional chemical reactions

Flávio Valadares P. Borges, Roberto Mioso, Luíz André A. Silva, José Maria Barbosa-Filho, Gabrielly Diniz Duarte and Luís Cezar Rodrigues

 Post-Graduate Program in Natural Products and Bioactives, Federal University of Paraíba, João Pessoa, 58051-900, PB, Brazil

Department of Chemistry, University of Las Palmas de Gran Canaria, Las Palmas de Gran Canaria, 35017, Spain

Department of Biotechnology, Federal University of Paraíba, João Pessoa, 58051-900, PB, Brazil

Post-Graduate Program in Development and Technological Innovation in Medicines, Federal University of Paraíba, João Pessoa, 58051-900, PB, Brazil

Abstract: Using classical reactions, the synthesis of seven natural esters was described, including for the first time the synthesis of four natural phenylpropanoid esters — compounds that have demonstrated promising bioactivity, proven by preliminary studies using samples obtained from natural sources. Applying the Wittig reaction, cis- and trans-bornyl ferulates were obtained, in an unusual manner, which established an alternative for the preparation of phenylpropanoid esters, especially in the synthesis of phenolic esters of tertiary alcohols such as the α- terpinyl trans-caffeate. The compounds obtained were identified and characterized by 1H-NMR and 13C-NMR spectroscopy.

Keywords:Wittig reaction; esterification; phenylpropanoid esters. ©2018 ACG Publication. All right reserved