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Identifier 000387779
Title Σύνθεση πολύπλοκων σκελετών φυσικών προϊόντων μέσω φωτοξείδωσης απλών φουρανίων
Alternative Title Synthesis of complex natural product skeletons via photooxidation of simple furans
Author Αλεξοπούλου, Ιωάννα Αχιλλέα
Thesis advisor Βασιλικογιαννάκης, Γεώργιος
Reviewer Στρατάκης, Εμμανουήλ
Βουρλούμης, Διονύσιος
Ορφανόπουλος, Μιχάλης
Κατερινόπουλος, Χαράλαμπος
Σμόνου, Ιουλία
Μήλιος, Κωνσταντίνος
Abstract The synthesis of Meyer’s bicyclic lactams is described in the first chapter of this thesis. These bicyclic lactams have been utilized in the synthesis of a wide variety of natural and non-natural products with biological activity. Α novel approach is reported, in which a singlet-oxygen-initiated reaction cascade is used. This reaction begins from simple furans, which can be easily functionalized, and allows direct access to highly substituted bicyclic lactams. The synthesis of 4-hydroxy- and 4-methoxy-2-cyclopentenones is described in the second chapter of this thesis. These structures are important precursors for the synthesis of many bioactive natural products. A general methodology is introduced for the onepot transformation of suitably substituted furans into the desired structures. Singlet oxygen initiates complex cascade reaction sequences which afford 4-hydroxy-2- cyclopentenones. The synthesis of the [6,5,5]-fused-spiroketal skeleton of natural products Macrodasines A, B, C and G is described in the third chapter of this thesis. A cascade sequence initiated by a [4+2]-cycloaddition of singlet oxygen (1O2) to a suitably substituted furan is followed by two sequential cyclizations.
Language Greek
Subject Cyclopentenones
Domino reaction
Furan oxidation
Nitrogen heterocycles
Singlet oxygen
Διεγερμένο μοριακό οξυγόνο
Ετεροκυκλικές ενώσεις αζώτου
Ντόμινο αντιδράσεις
Οξείδωση φουρανίων
Issue date 2014-10-10
Collection   Faculty/Department--Faculty of Sciences and Engineering--Department of Chemistry--Doctoral theses
  Type of Work--Doctoral theses
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