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Identifier

000455616

Title

Σύνθεση αναλόγων της κολιμπακτίνης μέσω φωτοκαταλυτικής αντίδρασης κυκλοπροπανίωσης

Alternative Title

Synthesis of colibactin warhead analogues via photocatalytic cyclopropanation reaction

Author

Γκριμπούρα, Νεφέλη Χ.

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Abstract

In Chapter 1 of this master thesis, a brief introduction about the general methods of the cyclopropane ring synthesis using diiodomethane and diazo-compounds as carbene sources is presented. Besides, the classical methods, the synthesis of cyclopropanes via photocatalysis in the presence or absence of transition metals using the same reagents is also described. Moreover, the uses of organic dye eosin in organic synthesis are described. Finally, the structure of colibactin and it’s genotoxic action are discussed. In Chapter 2 a new and green method for the photocatalytic synthesis of cyclopropane rings from 5-ylidene-1H-pyrrol-2(5H)-ones, which are structural analogs of colibactin warhead is presented. Two different 1,1-dihalides are used for the photocatalysis, diiodomethane and ethyl dibromoacetate. The organic dye eosin is used as the photocatalyst. Also, the one pot synthesis of colibactin warhead analogs starting from substituted furans is described. In Chapter 3 all the experimental procedures for the synthesis of the substituted furans, 5-ylidene-1H-pyrrol-2(5H)-ones and the desired final cyclopropyl products are described. In Chapter 4 all the NMR spectroscopy data of the synthesized compounds are given.

Language

Greek, English

Subject

Colibactin warhead analogues

Eosin, diiodomethane

Ethyl dibromoacetate

Διβρωμοοξικός αιθυλεστέρας

Διιωδομεθάνιο

Δομικά ανάλογα της κολιμπακτίνης

Εωσίνη

Issue date

2023-07-27