Event Title

Studies towards the total synthesis of Lobophorol A

Presenter Information

Summer Hackenburg

Faculty Advisor

Elizabeth Valentin

Start Date

24-4-2018 12:00 PM

End Date

24-4-2018 1:00 PM

Description

Lobophorol A is metabolite recently isolated from the marine algae of Lobophora variegata that demonstrated potential antibacterial activity. Like many natural products, total synthesis remains the best means to obtain enough amounts of these compounds for further biological testing. In order to develop a general synthetic route to lobophorol A, several derivatives were synthesized lacking the external acetyl group to determine if this acetyl group was imperative for activity of lobophorol A derivatives. A modified synthetic approach was used with a 1,4 Michael addition of diethyl malonate to a,b-unsaturated ketones. These reactions induced a ring closing and, after hydrolysis and decarboxylation, lead to the desired derivatives. Further studies will be conducted with other derivatives with different substituents as the aliphatic side chain to test how they affect the activity against S. aureus. The derivatives that were successfully synthesized will be tested in the near future for their biological activity against S. aureus and these activities will be reported at a future date.

This document is currently not available here.

Share

COinS
 
Apr 24th, 12:00 PM Apr 24th, 1:00 PM

Studies towards the total synthesis of Lobophorol A

Lobophorol A is metabolite recently isolated from the marine algae of Lobophora variegata that demonstrated potential antibacterial activity. Like many natural products, total synthesis remains the best means to obtain enough amounts of these compounds for further biological testing. In order to develop a general synthetic route to lobophorol A, several derivatives were synthesized lacking the external acetyl group to determine if this acetyl group was imperative for activity of lobophorol A derivatives. A modified synthetic approach was used with a 1,4 Michael addition of diethyl malonate to a,b-unsaturated ketones. These reactions induced a ring closing and, after hydrolysis and decarboxylation, lead to the desired derivatives. Further studies will be conducted with other derivatives with different substituents as the aliphatic side chain to test how they affect the activity against S. aureus. The derivatives that were successfully synthesized will be tested in the near future for their biological activity against S. aureus and these activities will be reported at a future date.