A Total Synthesis Approach Towards a Novel Furoquinolinone Natural Product Isolated from the Rutaceae Family

Abstract

Furo- and pyranoquinolinone containing natural products have been isolated from the Rutaceae family sine the 1960’s1 and 1970’s2 and have shown to exhibit a range of biological activities such as antifungal, antibacterial, antiviral, antimicrobial, antimalarial, insecticidal, antineoplastic, antidiuretic, antiarrythmic and sedative properties. Due to this, synthetic strategies have been developed to afford some of the selected natural products. In the course of extracting natural products at Natural Product Discovery (Brisbane, QLD, Australia), one natural product, 1.01, was isolated from the species Euodia asteridala (Rutaceae) and was of interest because of the ongoing screening of that class of molecules and the synthetic challanges involved. The natural product 1.01 consists of a furoquinolinone core with a cyclopropane ring fused onto the C2-C3 carbons of the furan ring, and a gem dimethyl functionality off the quarternary carbon of the cyclopropane ring. This thesis explores a total synthesis approach to compound 1.01, with focus on a new synthetic strategy to afford the furoquinolinone core structure as a key intermediate.