Synthetic studies on 1-azabicyclo[5.3.0]decane alkaloids

Abstract

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.