Batch and Continuous Flow Total Synthesis of Cannabidiol

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Braga, Felipe C. ; da Silva, Felipe L. N. ; Ramos, Tiago de O. ; Rosa, Joao G. H. ; Araujo, Erica de A. ; Junior, Nelson F. C. ; Wendler, Edison P. ; Beatriz, Adilson ; de Souza, Rodrigo O. M. A. ; Brocksom, Timothy J. ; de Oliveira, Kleber T.

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRY-AN ASIAN JOURNAL; v. 19, n. 20, p. 7-pg., 2024-10-16.

Resumo

Herein, we present a comprehensive total synthesis of cannabidiol integrating both batch and continuous flow conditions. Our approach is planned to streamline the synthesis of olivetolic acid derivatives and utilize an enantiomerically pure monoterpene moiety obtained from naturally occurring (R)-(+)-limonene by photocatalysis. Key reactions, including the synthesis of olivetolic ester and a Friedel-Crafts alkylation, are successfully adapted to continuous flow, resulting in improved yields and selectivities. This study not only offers a scalable and efficient route for cannabidiol synthesis but also contributes to the synthetic approaches to access cannabinoids (diversity synthesis), with potential applications in medicinal and industrial contexts. We present a batch and continuous-flow synthetic approach to produce Cannabidiol. Our route is based on the total synthesis of Cannabidiol, where the monoterpene portion is derived from biomass (orange peels) and the resorcinol portion is obtained in a two-step synthesis. This study offers a scalable and efficient route for the synthesis of Cannabidiol, providing various benefits compared to extraction from Cannabis sativa, such as greater control of impurities, better quality control, and easier regulation. image (AU)

• Processo FAPESP: 13/07276-1 - CEPOF - Centro de Pesquisa em Óptica e Fotônica
• Beneficiário: Vanderlei Salvador Bagnato
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 20/06874-6 - Aplicações das metodologias e tecnologias de síntese em regime de fluxo contínuo desenvolvidas no LQBO-UFSCar na preparação de moléculas com atividades biológicas e IFAs
• Beneficiário: Kleber Thiago de Oliveira
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 23/04020-8 - Síntese de IFAs utilizando-se tecnologias facilitadoras: abordagens envolvendo eletrossíntese e fotocatálise em regime de fluxo contínuo
• Beneficiário: Kleber Thiago de Oliveira
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 21/06110-9 - Aplicações da química de fluxo contínuo na síntese de Insumos Farmacêuticos Ativos (IFAs): canabidiol, fentanil e ibuprofeno
• Beneficiário: Felipe Camargo Braga
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado