Studies on photooxygenation reactions and chemical transformations in (+)-(alfa)-pinene to (-)-pinocarvone and (-)-aritasone under continuous flow conditions

• Grant number: 20/04114-4
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: October 01, 2020
• End date: September 30, 2023
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Gabriel Hiroshi Seki Rosa
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

This undergraduate sub-project is part of the projects in progress at LQBO which are related to our research line - organic reactions developed/photocatalyzed under continuous flow conditions.Specifically, the studies proposed here are: about the semi-synthesis of the natural product (-)-pinocarvone starting from (+)-pinene using photo-oxygenations promoted by porphyrins with subsequent rearrangements of the hydroperoxide intermediate. Studies involving this transformation are described in the literature, however, with low efficiency/productivity. Thus, we propose the use of continuous condition protocols developed in our laboratory to carry it out (reactors developed in our laboratory). We believe that some optimizations under continuous flow conditions should bring safety, scalability and ease in obtaining (-)-pinocarvone. Additionally, we intend to study some transformations that include the continuous synthesis of the natural product (-)-aritasone under extreme conditions (Novel Process Window) of temperature and pressure (Figure i). With this project we aim to provide to the undergraduate student training and contact with processes and reactions under continuous conditions so that in later stages of their training they can evolve and apply these technologies to solve problems in both synthesis and process with high level of difficulties. It is important to highlight that, despite the previous literature on the reactions proposed here, with these studies we should also move forward in terms of novelty, using continuous and optimized conditions for obtaining (-)-pinocarvone as well as (-)-aritasone.

Scientific publications

(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)

ROSA, GABRIEL H. S.; SANTOS, THIAGO I. S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.. Diverse continuous photooxygenation reactions of (+) and (-)-alpha-pinenes to the corresponding pinocarvones or trans-pinocarveols. REACTION CHEMISTRY & ENGINEERING, v. N/A, p. 8-pg., 2022-12-05. (20/06874-6, 19/27176-8, 13/07276-1, 20/04114-4)

FRANCO, MARCELO S.; SILVA, RODRIGO C.; ROSA, GABRIEL H. S.; FLORES, LARA M.; DE OLIVEIRA, KLEBER T.; DE ASSIS, FRANCISCO F.. Synthesis of the Brivaracetam Employing Asymmetric Photocatalysis and Continuous Flow Conditions. ACS OMEGA, v. 8, n. 25, p. 9-pg., 2023-06-14. (20/06874-6, 19/27176-8, 20/04114-4, 18/00879-6)