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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

Κυκλοπεντενόνες

Ντόμινο αντιδράσεις