JYX > Opinnäytteet > Väitöskirjat > View Item
Synthetic studies on 1-azabicyclo[5.3.0]decane alkaloids
The first chapter introduces the reader to the concept of natural product total synthesis and its importance to chemistry, other sciences, and society. The second chapter reviews the chemistry of natural products containing 1-azabicyclo[5.3.0]decane motifs. This bicyclic motif and the natural products related to it, have been a continuous source of synthetic inspiration over the last decades. The second chapter of the thesis reviews the strategies and tactics developed. The third chapter covers the author’s total synthesis of stemoamide, a 1-azabicyclo[5.3.0]decane motif containing alkaloid. Additionally, two diastereomers of stemoamide were synthesized, allowing their structural reassignment. Tentative studies towards a divergent route to other stemona alkaloids from a key precursor were also carried out. The fourth chapter targets another 1-azabicyclo[5.3.0]decane alkaloid, cephalotaxine. These are the results of a four-month exchange to the group of Prof. Peter Somfai at Lund University. After various challenges, a short and facile formal total synthesis relying on a cascade cyclization was developed. The fifth chapter briefly restates the main conclusions of chapters two, three and four, and contemplates on the future of the field. Chapters six and seven contain experimental and computational details, respectively. ...
PublisherUniversity of Jyväskylä
ISSN Search the Publication Forum0357-346X
MetadataShow full item record
- Väitöskirjat 
Showing items with similar title or keywords.
Formal synthesis of ent-Cephalotaxine using a one-pot Parham-aldol sequence Siitonen, Juha; Yu, Lu; Danielsson, Jakob; Gregorio, Giovanni Di; Somfai, Peter (American Chemical Society, 2018)A short formal synthesis of ent-Cephalotaxine is achieved. The approach features a new Lewis acid mediated [2,3]-Stevens rearrangement of N-allylated prolineamide to generate a key quaternary stereogenic center. Additionally, ...
A novel synthetic approach to pyran-2,4-dione scaffold production : microwave-assisted dimerization, cyclization, and expeditious regioselective conversion into β-enamino-pyran-2,4-diones Sarhan, Ahmed A.M.; Haukka, Matti; Barakat, Assem; Boraei, Ahmed T.A. (Elsevier, 2020)Here, we report a novel, green, simple, low-cost, and rapid methodology for the high-yield production of pyran-2,4-dione scaffolds under microwave irradiation. Regio- and stereoselective conversions of β-diketone systems ...
Towards Controlled Synthesis of Water-Soluble Gold Nanoclusters : Synthesis and Analysis Sokolowska, Karolina; Malola, Sami; Lahtinen, Manu; Saarnio, Ville; Permi, Perttu; Koskinen, Katariina; Jalasvuori, Matti; Häkkinen, Hannu; Lehtovaara, Lauri; Lahtinen, Tanja (American Chemical Society, 2019)Water-soluble gold nanoclusters with well-defined molecular structures and stability possess particular biophysical properties making them excellent candidates for biological applications as well as for fundamental ...
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution Axelsson, Anton; Westerlund, Mathias; Zacharias, Savannah C.; Runemark, August; Haukka, Matti; Sundén, Henrik (Wiley, 2021)An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, ...
Water-Soluble Cuprizone Derivative: Synthesis, Characterization, and in Vitro Studies Fries, Martin; Mertens, Meike; Teske, Nico; Kipp, Markus; Beyer, Cordian; Willms, Thomas; Valkonen, Arto; Rissanen, Kari; Albrecht, Markus; Clarner, Tim (American Chemical Society, 2019)The cuprizone mouse model is one of the most accepted model systems for the investigation of oligodendrocyte degeneration, a process critically involved in the pathogenesis of diseases such as multiple sclerosis or ...