We review the emerging use of flow technologies for circular chemistry and material manufacturing... more We review the emerging use of flow technologies for circular chemistry and material manufacturing, highlighting advances, challenges, and future directions.
A 5-steps continuous flow synthesis of lesinurad is provided and delivers this API in 68% overall... more A 5-steps continuous flow synthesis of lesinurad is provided and delivers this API in 68% overall yield.
The combination of a new NADES system and MW irradiation allowed for the preparation of HMF in hi... more The combination of a new NADES system and MW irradiation allowed for the preparation of HMF in high yields and in short reaction times.
An integrated continuous flow process for the synthesis of 3-thio-1,2,4-triazoles is reported. A ... more An integrated continuous flow process for the synthesis of 3-thio-1,2,4-triazoles is reported. A small library of 18 compounds was prepared in just 48 minutes of residence time in moderate to excellent yields.
The generation and use of acyl ketenes under continuous flow reaction conditions is reported. Sev... more The generation and use of acyl ketenes under continuous flow reaction conditions is reported. Several reaction classes of these reactive intermediates have been studied. Under zero headspace conditions, a ketone exchange process is possible between volatile ketones. The process can be readily scaled to deliver gram quantities of product.
Revista dos Trabalhos de Iniciação Científica da UNICAMP
Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These mo... more Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These molecules present a β-hydroxyoctanoic acid coupled to well-defined amino acid or α-hydroxy acid residue sequences and have been isolated from the marine cyanobacteria Okeania sp. in Japan, 2017.1 Kohamamides chemical structures were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry analyses. Isolated kohamamides showed pronounced cytotoxic activity against cell lines of human leukemia, being kohamamide B the most active (IC50 = 6.0 µM). In this context, we propose the first total syntheses of Kohamamides A, B e C, in a total of 15 steps. The synthetic retro analysis consisted in the fragmentation of main blocks, 4 and 5. Initially, the intermediates 2 and 3 were obtained with high yield (2, 79% for 2 steps, and 3 with quantitative yield) and the synthesis of fragment 11 in good yield (68%). Additional efforts will be directed to the synthesis of intermediate 1, followed ...
Revista dos Trabalhos de Iniciação Científica da UNICAMP
The synthesis of monomers for the production of novel green polymers was evaluated in continuous ... more The synthesis of monomers for the production of novel green polymers was evaluated in continuous flow conditions using terpenes as dienes and maleic anhydride as dienophile for the [4+2] Diels-Alder cycloaddition reaction. The hydrogenation reaction was also evaluated to prevent the retro-Diels-Alder and to expand the reactional scope by producing adducts with distinct characteristics of structures and reactivity. Fourteen different monomers were obtained in good yields in flow regime.
Revista dos Trabalhos de Iniciação Científica da UNICAMP
Cacospongia sp. is a species of marine sponge that produces labdane-class diterpens known as Caco... more Cacospongia sp. is a species of marine sponge that produces labdane-class diterpens known as Cacofurans A and B, which show cytotoxic activity in vitro. In this work, we present the synthetic pathway of Cacofurans A and B in ten and nine steps, respectively. Five steps of the synthetic proposal were completed, with 25% overall yield, including the formation of a five-membered ring using the Suárez reaction. After the completion of the total synthesis, the cytotoxic potential of Cacofurans A and B will be evaluated.
We report the development of a continuous flow approach for the preparation of two bio-derived mo... more We report the development of a continuous flow approach for the preparation of two bio-derived monomer libraries. A small range of terpenes; ocimene, myrcene, α-terpinene, α-phellandrene, isoprene, and farnesene, have...
We present a comprehensive review of the advent and impact of continuous flow chemistry with rega... more We present a comprehensive review of the advent and impact of continuous flow chemistry with regard to the synthesis of natural products and drugs, important pharmaceutical products and definitely responsible for a revolution in modern healthcare. We detail the beginnings of modern drugs and the large scale batch mode of production, both chemical and microbiological. The introduction of modern continuous flow chemistry is then presented, both as a technological tool for enabling organic chemistry, and as a fundamental research endeavor. This part details the syntheses of bioactive natural products and commercial drugs.
The production of compounds known as building blocks from renewable resources has aroused much in... more The production of compounds known as building blocks from renewable resources has aroused much interest from the scientific community in the recent years. Building blocks are molecules that exhibit in most cases multiple functional groups and offer unique possibilities to be chemically or biologically transformed into high added-value compounds. Some examples of these include biopolymers, biofuels, solvents, and biochemicals. Among the examples of building blocks, 5-(hydroxymethyl)furfural (5-HMF) is presented as one of the most studied compound in recent years due to its potential as raw material for preparation of bio-based chemicals. In this context, in the proposed review, the recent synthetic methodologies for 5-HMF production from renewable resources will be presented, as well as the application of 5-HMF as raw material for liquid biofuels and biopolymers production.
RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics a... more RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics and kinetics aspects of the hydroamination reaction, recent advancements on this field for non-activated alkenes, alkynes and allenes, employing transition metal catalysis or organocatalysis, including activation by hydrogen bonding or Brønsted acids. Selected syntheses that contain a strategic hydroamination step will be discussed, and advancements on the asymmetric version will also be highlighted. The full coverage of scientific activity about hydroamination is beyond this review, therefore the examples presented are from the last ten years, except when there are historical reasons for the discussion of previous works.
We review the emerging use of flow technologies for circular chemistry and material manufacturing... more We review the emerging use of flow technologies for circular chemistry and material manufacturing, highlighting advances, challenges, and future directions.
A 5-steps continuous flow synthesis of lesinurad is provided and delivers this API in 68% overall... more A 5-steps continuous flow synthesis of lesinurad is provided and delivers this API in 68% overall yield.
The combination of a new NADES system and MW irradiation allowed for the preparation of HMF in hi... more The combination of a new NADES system and MW irradiation allowed for the preparation of HMF in high yields and in short reaction times.
An integrated continuous flow process for the synthesis of 3-thio-1,2,4-triazoles is reported. A ... more An integrated continuous flow process for the synthesis of 3-thio-1,2,4-triazoles is reported. A small library of 18 compounds was prepared in just 48 minutes of residence time in moderate to excellent yields.
The generation and use of acyl ketenes under continuous flow reaction conditions is reported. Sev... more The generation and use of acyl ketenes under continuous flow reaction conditions is reported. Several reaction classes of these reactive intermediates have been studied. Under zero headspace conditions, a ketone exchange process is possible between volatile ketones. The process can be readily scaled to deliver gram quantities of product.
Revista dos Trabalhos de Iniciação Científica da UNICAMP
Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These mo... more Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These molecules present a β-hydroxyoctanoic acid coupled to well-defined amino acid or α-hydroxy acid residue sequences and have been isolated from the marine cyanobacteria Okeania sp. in Japan, 2017.1 Kohamamides chemical structures were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry analyses. Isolated kohamamides showed pronounced cytotoxic activity against cell lines of human leukemia, being kohamamide B the most active (IC50 = 6.0 µM). In this context, we propose the first total syntheses of Kohamamides A, B e C, in a total of 15 steps. The synthetic retro analysis consisted in the fragmentation of main blocks, 4 and 5. Initially, the intermediates 2 and 3 were obtained with high yield (2, 79% for 2 steps, and 3 with quantitative yield) and the synthesis of fragment 11 in good yield (68%). Additional efforts will be directed to the synthesis of intermediate 1, followed ...
Revista dos Trabalhos de Iniciação Científica da UNICAMP
The synthesis of monomers for the production of novel green polymers was evaluated in continuous ... more The synthesis of monomers for the production of novel green polymers was evaluated in continuous flow conditions using terpenes as dienes and maleic anhydride as dienophile for the [4+2] Diels-Alder cycloaddition reaction. The hydrogenation reaction was also evaluated to prevent the retro-Diels-Alder and to expand the reactional scope by producing adducts with distinct characteristics of structures and reactivity. Fourteen different monomers were obtained in good yields in flow regime.
Revista dos Trabalhos de Iniciação Científica da UNICAMP
Cacospongia sp. is a species of marine sponge that produces labdane-class diterpens known as Caco... more Cacospongia sp. is a species of marine sponge that produces labdane-class diterpens known as Cacofurans A and B, which show cytotoxic activity in vitro. In this work, we present the synthetic pathway of Cacofurans A and B in ten and nine steps, respectively. Five steps of the synthetic proposal were completed, with 25% overall yield, including the formation of a five-membered ring using the Suárez reaction. After the completion of the total synthesis, the cytotoxic potential of Cacofurans A and B will be evaluated.
We report the development of a continuous flow approach for the preparation of two bio-derived mo... more We report the development of a continuous flow approach for the preparation of two bio-derived monomer libraries. A small range of terpenes; ocimene, myrcene, α-terpinene, α-phellandrene, isoprene, and farnesene, have...
We present a comprehensive review of the advent and impact of continuous flow chemistry with rega... more We present a comprehensive review of the advent and impact of continuous flow chemistry with regard to the synthesis of natural products and drugs, important pharmaceutical products and definitely responsible for a revolution in modern healthcare. We detail the beginnings of modern drugs and the large scale batch mode of production, both chemical and microbiological. The introduction of modern continuous flow chemistry is then presented, both as a technological tool for enabling organic chemistry, and as a fundamental research endeavor. This part details the syntheses of bioactive natural products and commercial drugs.
The production of compounds known as building blocks from renewable resources has aroused much in... more The production of compounds known as building blocks from renewable resources has aroused much interest from the scientific community in the recent years. Building blocks are molecules that exhibit in most cases multiple functional groups and offer unique possibilities to be chemically or biologically transformed into high added-value compounds. Some examples of these include biopolymers, biofuels, solvents, and biochemicals. Among the examples of building blocks, 5-(hydroxymethyl)furfural (5-HMF) is presented as one of the most studied compound in recent years due to its potential as raw material for preparation of bio-based chemicals. In this context, in the proposed review, the recent synthetic methodologies for 5-HMF production from renewable resources will be presented, as well as the application of 5-HMF as raw material for liquid biofuels and biopolymers production.
RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics a... more RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics and kinetics aspects of the hydroamination reaction, recent advancements on this field for non-activated alkenes, alkynes and allenes, employing transition metal catalysis or organocatalysis, including activation by hydrogen bonding or Brønsted acids. Selected syntheses that contain a strategic hydroamination step will be discussed, and advancements on the asymmetric version will also be highlighted. The full coverage of scientific activity about hydroamination is beyond this review, therefore the examples presented are from the last ten years, except when there are historical reasons for the discussion of previous works.
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Papers by Julio Pastre