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Expanding the use of carrot bits (Daucus carota) in organic synthesis - applications in total synthesis of bioactive molecules, novel substrates and the development of a scale-up methodology

Grant number: 17/18007-2
Support type:Regular Research Grants
Duration: February 01, 2018 - April 30, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Alvaro Takeo Omori
Grantee:Alvaro Takeo Omori
Home Institution: Centro de Ciências Naturais e Humanas (CCNH). Universidade Federal do ABC (UFABC). Ministério da Educação (Brasil). Santo André , SP, Brazil

Abstract

This proposal aims to expand the applications of the use of carrot pieces in organic synthesis. This edible plant is used as a biocatalyst in reduction reactions of prochiral ketones, leading to alcohols with excellent values of enantiomeric excess and good conversion rates. Our research group demonstrated that this technique can be applied both in total synthesis (talampanel) and in synthetic methodologies (one-pot with Click Chemistry, use of surfactants and screening of carrot species). Due to the ease of execution, the low cost and the absence of aseptic conditions, this method was also applied for education purposes, as a undergraduate experiment to be applied in Organic Chemistry and Green Chemistry courses.In spite of its limitations regarding the reactivity restricted to aldehydes and ketones and the high mass of the biocatalyst, the proposal here is precisely to show that this plant is a versatile methodology in organic synthesis. In this case, we propose the use of carrot as a key step in the total asymmetric synthesis of bioactive compounds, such as etomidate (1) and duloxetine (2). In addition, reactions involving new substrates such as dihydro-3(2H)-furanone (6) e dihydro-3(2H)-tiophenone (7) and a proposal to improve the experimental conditions aiming to increase the scale of the reaction will also be presented. (AU)