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Identifier 000406663
Title Σύνθεση βιοδραστικών ενώσεων με τη χρήση του οξυγόνου απλής κατάστασης
Alternative Title Synthesis of bioactive compounds using singlet oxygen
Author Κοτζαμπασάκη, Βασιλική
Thesis advisor Στρατάκης, Μανώλης
Reviewer Ορφανόπουλος, Μιχαήλ
Κατερινόπουλος, Χαράλαμπος
Βασιλικογιαννάκης, Γεώργιος
Σμόνου, Ιουλία
Ηλιόπουλος, Αριστείδης
Σπύρος, Απόστολος
Abstract In the current Thesis, the application of [4+2] cycloaddition reaction of singlet oxygen with furans is presented, as a crucial step, not only in the development of new methodologies, but also in the synthesis of natural products. The results can be summarized as follows: - The design and synthesis of novel non-peptidic molecules, potent AVPI tetrapeptide-mimics, found in Smac/Diablo protein, are reported. This protein has the ability to provoke apoptosis (normal programmed cell death) in human cells, through binding of its N-terminus tetrapeptide (AVPI) to the human X-linked inhibitors of apoptosis proteins (XIAPs). The motif of Meyers bicyclic lactams could potentially act as an AVPI mimic, employing as a key step in its synthesis, the photooxidation reaction of simple furan substrates. The applied synthetic method offers the possibility of developing a small library of compounds for biological evaluation. - A new, exceptionally efficient methodology for the regioselective and quantitative synthesis of γ-hydroxybutenolides was developed, through photooxygenation of 2-thiophenyl-substituted furans. The thiophenyl moiety directs the formation of γ-hydroxybutenolides. This conversion is proposed to occur through radical scission of the endoperoxide formed through [4+2] cycloaddition of 2-thiophenyl furans with 1Ο2. - The total synthesis of the natural product (+)-yaoshanenolide B is presented for the first time in literature, employing as a key step an endo and highly selective Diels-Alder reaction, based on a biosynthetic scenario. Through completion of this synthetic route, we revised the proposed structure of yaoshanenolide B to one of its diastereomers instead.
Language Greek
Subject (+)-yaoshanenolide B
2-thiophenyl furans
2-θειοφαίνυλο φουράνια
Bicyclic γ-lactams
Biomimetic synthesis
Diels-Alder reaction
Furan photoxidation
Non-peptidic AVPI-mimics
Singlet oxygen
Smac/Diablo, AVPI
Smac/Diablo, AVPI
Αντίδραση Diels-Alder
Βιομιμητική σύνθεση
Διεγερμένο μοριακό οξυγόνο απλής κατάστασης (1Ο2)
Δικυκλικές γ-λακτάμες
Μη πεπτιδικές ενώσεις-μιμητες AVPI
Φωτοξείδωση φουρανίων
Issue date 2017-03-14
Collection   Faculty/Department--Faculty of Sciences and Engineering--Department of Chemistry--Doctoral theses
  Type of Work--Doctoral theses
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