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Identifier |
000388117 |
Title |
Σύνθεση δισπειροκεταλών και γ-Λακταμών μέσω φωτοξείδωσης απλών φουρανίων |
Alternative Title |
Synthesis of bis-spiroketals and γ-Lactams via photooxidation of simple furans |
Author
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Τριανταφυλλάκης, Μύρωνας
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Thesis advisor
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Βασιλικογιαννάκης, Γεώργιος
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Reviewer
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Ορφανόπουλος, Μιχαήλ
Στρατάκης, Εμμανουήλ
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Abstract |
In the following work, there is extensive discussion regarding the procedures
followed for the synthesis of bis-spiroketals and γ-lactams from readily accessible
furan substrates.
In Chapter 1 the synthesis of the ABCD-ring skeleton of the Azaspiracids is described
starting from a simple furan. In the preliminary experiments, the outcome of the
reaction sequence for a simple system (bearing two hydroxyl groups that might
compete at the ketalization stage) was studied. It was found that the reaction
proceeded smoothly, affording the [6,5,5]-spiroketal as a sole product. In order to get the desired reaction, therefore, the γ-hydroxyl group was efficiently
protected, constructing the desired D-ring at the same time. The final bis-spiroketal
system was synthesized in one synthetic operation from either one of two possible,
suitably functionalized, furan substrates. In Chapter 2 the methodology that was utilized for the synthesis of a novel
mimic of the AVPI tetrapeptide, found in Smac/DIABLO protein is explained. This
protein has the ability to regulate apoptosis in cells, with the AVPI having a major
role in the whole process. It was proposed that a synthetic drug, fulfilling structural
requirements, might mimic the endogenous tetrapeptide.
A Meyers bicyclic lactam could potentially act as an AVPI mimic. It was synthesized
based on a short and effective strategy, in which the key step is the photooxidation
of a furan substrate. The synthetic method that was employed is quite versatile, offering the possibility of
developing a small library of compounds. These compounds will be sent for
biological evaluation.
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Language |
Greek |
Subject |
AVPI |
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Apoptosis |
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Azaspiracids |
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Cell death |
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Polyoxygenated natural products |
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Singlet oxygen |
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Smac/DIABLO |
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Sustainable chemistry |
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Απόπτωση |
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Βιώσιμη χημεία |
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Διεγερμένο μοριακό οξυγόνο |
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Δισπιροκεταλικές ενώσεις |
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Κυτταρικός θάνατος |
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Πολυοξυγονομένα φυσικά προϊόντα |
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γ-λακτάμες |
Issue date |
2014-11-21 |
Collection
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School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses
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Type of Work--Post-graduate theses
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Permanent Link |
https://elocus.lib.uoc.gr//dlib/8/d/9/metadata-dlib-1415005757-520862-14301.tkl
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Views |
250 |