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Identifier

000388117

Title

Σύνθεση δισπειροκεταλών και γ-Λακταμών μέσω φωτοξείδωσης απλών φουρανίων

Alternative Title

Synthesis of bis-spiroketals and γ-Lactams via photooxidation of simple furans

Author

Τριανταφυλλάκης, Μύρωνας

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Ορφανόπουλος, Μιχαήλ
Στρατάκης, Εμμανουήλ

Abstract

In the following work, there is extensive discussion regarding the procedures followed for the synthesis of bis-spiroketals and γ-lactams from readily accessible furan substrates. In Chapter 1 the synthesis of the ABCD-ring skeleton of the Azaspiracids is described starting from a simple furan. In the preliminary experiments, the outcome of the reaction sequence for a simple system (bearing two hydroxyl groups that might compete at the ketalization stage) was studied. It was found that the reaction proceeded smoothly, affording the [6,5,5]-spiroketal as a sole product. In order to get the desired reaction, therefore, the γ-hydroxyl group was efficiently protected, constructing the desired D-ring at the same time. The final bis-spiroketal system was synthesized in one synthetic operation from either one of two possible, suitably functionalized, furan substrates. In Chapter 2 the methodology that was utilized for the synthesis of a novel mimic of the AVPI tetrapeptide, found in Smac/DIABLO protein is explained. This protein has the ability to regulate apoptosis in cells, with the AVPI having a major role in the whole process. It was proposed that a synthetic drug, fulfilling structural requirements, might mimic the endogenous tetrapeptide. A Meyers bicyclic lactam could potentially act as an AVPI mimic. It was synthesized based on a short and effective strategy, in which the key step is the photooxidation of a furan substrate. The synthetic method that was employed is quite versatile, offering the possibility of developing a small library of compounds. These compounds will be sent for biological evaluation.

Language

Greek

Subject

AVPI

Apoptosis

Azaspiracids

Cell death

Polyoxygenated natural products

Singlet oxygen

Smac/DIABLO

Sustainable chemistry

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