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Identifier

000397556

Title

Σύνθεση του ABCDE πολυκυκλικού σκελετού των φυσικών προϊόντων Pectenotoxins και α,β-ακόρεστων γ-λακταμών με φωτοξείδωση φουρανίων

Alternative Title

Synthesis of the ABCDE-ring skeleton of the natural products the Pectenotoxins and α,β-unsaturated-γ-lactams by photooxidation of furans

Author

Κουριδάκη, Αντωνία Εμμ

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Κατερινόπουλος, Χαράλαμπος
Σμόνου, Ιουλία
Ορφανόπουλος, Μιχαήλ
Στρατάκης, Εμμανουήλ
Δημάδης, Κωνσταντίνος
Σπύρος, Απόστολος

Abstract

In the first chapter of this thesis, the chemistry of singlet oxygen is briefly described. The methods for generation of singlet oxygen and its reactions are presented, as well as, its applications in various scientific fields but especially in organic synthesis. In the second chapter, synthesis of the CDE and ABCDE-ring fragments of the natural products the pectenotoxins, is delineated. The synthetic plan for the C-ring, and its subsequent attachment to an appropriately substituted furan, is presented. Photooxidation of this substrate affords the complete CDE-ring section. In addition, the potential of singlet oxygen in synthesis is further investigated when a difuran precursor is photooxidized to furnish the more complex ABCDE-ring skeleton. The CDE and ABCDE-ring units were both synthesized in one synthetic operation, via complex cascade reaction sequences initiated by photooxidation of simple furans. In the third chapter, a general methodology is introduced for the one-pot transformation of furans into α,β-unsaturated γ-lactams via photooxidation, which uses methylene blue as photosensitizer. In addition, the catalytic redox properties of methylene blue invoked by this synthesis are examined and a possible mechanistic explanation is presented. The methodology was applied to a variety of furan substrates, affording structural motifs seen in a slew of natural products with significant biological activity.

Language

Greek

Subject

5- υλιδενοπυρρολ-2(5Η)-όνες

5-hydroxy-1H-pyrrol-2(5H)-ones

5-ylidenepyrrol-2(5H)- ones

5-υδροξυ-1Η-πυρρολ-2(5Η)-όνες

Methylene blue

Singlet oxygen

Διεγερμένο οξυγόνο

α,β- ακόρεστες γ-λακτάμες

Issue date