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

Grant number: 20/04114-4
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): October 01, 2020
Effective date (End): September 30, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Kleber Thiago de Oliveira
Grantee:Gabriel Hiroshi Seki Rosa
Home 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.