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Identifier

000397559

Title

Ανάπτυξη βιώσιμων συνθετικών τεχνολογιών του διεγερμένου μοριακού οξυγόνου. Πρώτες ολικές συνθέσεις των φυσικών προϊόντων Paracaseolide A και Pandamarine

Alternative Title

Development of sustainable synthetic technologies using singlet oxygen. First total syntheses of natural products Paracaseolide A and Pandamarine

Author

Νούτσιας, Δημήτριος Ι.

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Ορφανόπουλος, Μιχαήλ
Στρατάκης, Εμμανούλ
Κατερινόπουλος, Χαράλαμπος
Σμόνου, Ιουλία
Περγαντής, Σπυρίδων
Μήλιος, Κωνσταντίνος

Abstract

In Chapter 1, a set of new synthetic approaches towards the synthesis of the common BCDEF pentacyclic system from the natural products pinnatoxins and pteriatoxins, is described. There are two main ideas behind these approaches. In the first case, a series of difuran substrates were synthesized and tested for their participation in an unprecedented one pot reaction sequence that could potentially lead to the formation of BCDEF system in one synthetic operation. In the second case, a stepwise synthetic approach was designed that included two photoxidation sequences as key reactions. In Chapter 2, the first total synthesis of the paracaseolide A, a very unusual tetraquinane oxa-cage bislactone recently isolated from the mangrove Sonneratia paracaseolaris, is described. The final step and culmination of the eight step synthetic sequence is a [4+2] dimerization of a 4-hydroxybutenolide, generated by singlet oxygen-mediated oxidation of a furan precursor. In Chapter 3, a highly efficient and general singlet oxygen-initiated one pot transformation of readily accessible furans into tricyclic α,β-unsaturated γ-lactams. This useful set of transformations relies on exploiting not just the photosensitising ability of methylene blue, but also its redox catalytic properties; properties that have until now been virtually ignored in a synthetic context. Moreover, this methodology has been applied to the first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius. The key step of this extremely short (6 steps in total) and protecting group-free synthesis is a highly efficient cascade reaction sequence initiated by the photooxidation of an easily accessible and symmetric difuran precursor.

Language

Greek

Subject

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

5-υδρόξυ-1Η-πυρρολι-2(5Η)-νονες

6-hydroxy- 3(2H)-pyranones

6-υδροξυ-3(2Η)πυρανόνες

Alkaloids

Cascade reactions

Furan photooxidation

Ideal synthesis

Methylene blue