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Direct functionalization of bulky terpenes by cross-metathesis

Grant number: 19/18981-4
Support type:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): February 01, 2020
Effective date (End): July 31, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Dalmo Mandelli
Grantee:Luciana Sarmento Fernandes
Supervisor abroad: Cedric Fischmeister
Home Institution: Centro de Ciências Naturais e Humanas (CCNH). Universidade Federal do ABC (UFABC). Ministério da Educação (Brasil). Santo André , SP, Brazil
Local de pesquisa : Institut des Sciences Chimiques de Rennes (ISCR), France  
Associated to the scholarship:15/26787-2 - Valuation of natural products via Methathesis and epoxidation of alkenes, BP.DR

Abstract

Cyclic monoterpenes are important bio-sourced components present in the resin of pine and citrus trees and some of them are currently produced on an industrial scale especially by the fruit juice industry in Brazil. Therefore, any environmentally benign transformation of these terpenes into new useful products should have a strong impact in terms of sustainable economy. So far we were especially interested in the functionalization of (1S)-(-)-²-pinene and (S)-(-)-limonene, which are bulky terpenes featuring a terminal gem-disubstituted carbon-carbon double bond. It is noteworthy that these terpenes had been only scarcely involved in olefin metathesis transformations. During the period so far it was already identified an efficient procedure for the transformation of sterically hindered terpenes. We have found that functionalized terpenes can be produced by cross metathesis with symmetrical internal olefins as cross metathesis partners. Therefore, it would of great interest to extend the scope of this procedure to other terpenes and terpenoids compounds to get the full benefit of the research efforts already carried out at the Institut des Sciences Chimiques de Rennes (ISCR) in order to get a better understanding of the key parameters of these transformations taking advantage of all the infrastructure available and the expertise of the team of the Université de Rennes 1.