A Total Synthesis Approach Towards a Novel Furoquinolinone Natural Product Isolated from the Rutaceae Family
Griffith University, 2014
Doctor of Philosophy (PhD)
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.
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