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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

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)

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Scientific publications (5)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
MACHADO, NAIRA VIEIRA; OMORI, ALVARO TAKEO. Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots. BIOCATALYSIS AND BIOTRANSFORMATION, v. 39, n. 6, p. 475-480, NOV 2 2021. Web of Science Citations: 0.
HIGA, VANESSA M.; OMORI, ALVARO T. A Two Hour Synthesis of the Anti-Parkinson Drug Safinamide Methanesulfonate. Synlett, v. 32, n. 14 JUN 2021. Web of Science Citations: 0.
MACHADO, NAIRA VIEIRA; OMORI, ALVARO TAKEO. Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots. BIOCATALYSIS AND BIOTRANSFORMATION, JAN 2021. Web of Science Citations: 0.
VANESSA M. HIGA; WILLIAN S. ROCHA; MIRELA INÊS DE SAIRRE; ÁLVARO T. OMORI. Lipase-Mediated Dynamic Kinetic Resolution of 1-Phenylethanol Using Niobium Salts as Racemization Agents. Journal of the Brazilian Chemical Society, v. 32, n. 10, p. 1956-1962, Out. 2021. Web of Science Citations: 1.
ALVARO T. OMORI; MARINA G. CAPELETTO; DANIELA Y. YAMAMOTO; RONALDO E. DE OLIVEIRA FILHO. A RENEWABLE CATALYST FOR A RENEWABLE CHEMICAL: GRAM-SCALE CONVERSION OF FURFURAL TO FURFURYL ALCOHOL BY THE CARROT (Daucus carota). Química Nova, v. 43, n. 1, p. 32-36, Jan. 2020. Web of Science Citations: 0.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.