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Synthetic studies toward citrofulvicin : synthesis of the core ring system / Kalina O. Doytchinova-Weil.
- Format:
- Book
- Thesis/Dissertation
- Author/Creator:
- Doytchinova-Weil, Kalina O., author.
- Language:
- English
- Subjects (All):
- Chemistry.
- Mass spectrometry.
- Chloride.
- Oxidation.
- Nuclear magnetic resonance--NMR.
- Biosynthesis.
- Staphylococcus infections.
- Fractures.
- Scientific imaging.
- Chromatography.
- Potassium.
- Older people.
- Spinal cord.
- Natural products.
- Biological activity.
- Osteoporosis.
- Chemistry--Penn dissertations.
- Penn dissertations--Chemistry.
- Local Subjects:
- Chemistry.
- Mass spectrometry.
- Chloride.
- Oxidation.
- Nuclear magnetic resonance--NMR.
- Biosynthesis.
- Staphylococcus infections.
- Fractures.
- Scientific imaging.
- Chromatography.
- Potassium.
- Older people.
- Spinal cord.
- Natural products.
- Biological activity.
- Osteoporosis.
- Chemistry--Penn dissertations.
- Penn dissertations--Chemistry.
- Genre:
- Academic theses.
- Physical Description:
- 1 online resource (431 pages)
- Contained In:
- Dissertations Abstracts International 83-03B.
- Place of Publication:
- [Philadelphia, Pennsylvania] : University of Pennsylvania ; Ann Arbor : ProQuest Dissertations & Theses, 2021.
- Language Note:
- English
- System Details:
- Mode of access: World Wide Web.
- text file
- Summary:
- The polyketide natural product citrofulvicin, which was isolated in 2018, presents an intriguing synthetic target due to both the structural complexity of the octacyclic ring system, which contains a 1-hydroxy-2,4,6-trioxaadamantane ring, and the reported antiosteoporotic activity of citrofulvicin. Synthetic access to this natural product would allow for further biological evaluation. This dissertation describes the synthetic efforts toward citrofulvicin. An initial approach using an isoxazole ring as a protecting group for a β-diketone on a model system targeting the core ring system of citrofulvicin led to the formation of unexpected polycyclic pyridine-containing structures. An alternative approach using a dioxolane protecting group on the model system led to the development of a concise synthesis of the key intermediate for the proposed final intramolecular cyclization cascade. Due to the observed unexpected intramolecular reactivity of this intermediate, a thioketal blocking group was introduced, which allowed for the successful cyclization cascade to occur. Removal of the thioketal blocking group led to the core ring system of citrofulvicin, which only lacked the aromatic ring substituents. Thus, the core ring system was synthesized in nine steps from readily available materials and the developed synthetic route should translate to the synthesis of citrofulvicin with a suitably substituted aromatic starting material.
- Notes:
- Source: Dissertations Abstracts International, Volume: 83-03, Section: B.
- Advisors: Winkler, Jeffrey D.; Committee members: Molander, Gary A.; Chenoweth, David M.; Dailey, William P.
- Department: Chemistry.
- Ph.D. University of Pennsylvania 2021.
- Local Notes:
- School code: 0175
- ISBN:
- 9798535569420
- Access Restriction:
- Restricted for use by site license.
- This item must not be sold to any third party vendors.
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