This is a sub-project for a graduation course student which is related to our research line under development in the laboratory of Bioorganic Chemistry (LQBO) -photocatalysed reactions under continuous flow conditions mediated by porphyrinoids (FAPESP project 2015/21110-4).Herein, we propose studies on the semi-synthesis of the natural product Moracin M starting from resveratrol as starting material by using photooxygenation reactions mediated by porphyrins and a further thermal rearrangement. A previous study in batch conditions was described in the literature, however, with low yields, low selectivity and small scale (5 mg) as well. In this mentioned literature, it was observed a competition between the [4+2] and [2+2] processes while the singlet oxygen reacted with resveratrol. Thus, we believe that some optimizations under continuous flow conditions such temperature control, concentration, and the use of the tube-in-tube reactor will make this process more safe, scalable, and most importantly, selective ([4+2] versus [2+2]) for the synthesis of Moracin M. Additional protection of resveratrol will be studied aiming at the improvement of the selectivity, and also allow further experiments under basic catalysis in order to check the possibility of a Kornblum-DeLamare rearrangement. Therefore, mechanism studies are also desired in this project, specially of the thermal rearrangement from the endoperoxide to Moracin M.
News published in Agência FAPESP Newsletter about the scholarship: