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

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Author(s)
Primary Supervisor
Ripper, Justin
Other Supervisors
Quinn, Ron
Carroll, Anthony
Year published
2014
Metadata
Show full item recordAbstract
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 ...
View more >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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View more >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.
View less >
Thesis Type
Thesis (PhD Doctorate)
Degree Program
Doctor of Philosophy (PhD)
School
School of Biomolecular and Physical Sciences
Copyright Statement
The author owns the copyright in this thesis, unless stated otherwise.
Item Access Status
Public
Note
This thesis has been scanned.
Subject
Furoquinolinone
Rutaceae Family
Antifungal
Antiviral
Antibacteria
Antiarrythmic
Antimalarial