Towards a total synthesis of bazzanin K

by Christian Johann Rugen
Doctoral thesis
Date of Examination:2022-03-24
Date of issue:2022-05-31
Advisor:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Konrad Koszinowski
Referee:Prof. Dr. Lutz Ackermann
Referee:Dr. Daniel Janßen-Müller
Referee:Prof. Dr. Claudia Steinem
Referee:Dr. Michael John
Persistent Address: http://dx.doi.org/10.53846/goediss-9278

 

 

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Abstract

English

Bazzanin K is a natural product from the group of macrocyclic bis-bibenzyls which was isolated from the liverwort bazzania trilobata. This work is dedicated towards the development of a synthetic strategy with bazzanin K at the end. Similar macrocyclic bis-bibenzyls have been prepared and their literature known syntheses shall serve as an inspiration. In a first step, unsubstituted model substances were prepared successfully to test the viability of pi-acid catalysis for the synthesis of a phenanthrene motif and an intramolecular Wittig reaction for a macrocyclization as key steps in the total synthesis. For the preparation of bazzanin K four aromatic building blocks were prepared with a variety of different substitution patterns. Different synthetic strategies for the connection of these units were tested and important key intermediates were obtained.
Keywords: bazzanin K; total synthesis; pi-acid catalysis; cross coupling reaction; aromatic compound; macrocyclization; Wittig reaction; macrocyclic bis-bibenzyl