ISBN 9783843939737

978-3-8439-3973-7, Reihe Organische Chemie

Maike H. Wahl
A [2+2] Photocycloaddition-Fragmentation Approach for cis-Fused Lycorine-type Natural Product Synthesis

229 Seiten, Dissertation Technische Universität München (2019), Softcover, A5

Zusammenfassung / Abstract

Members of the Amaryllidaceae alkaloid family exhibit a unique cis-junction between the B and C ring being challenging targets for enantioselective total synthesis. By considering cyclobutanes not as products but rather as reactive intermediates, a [2+2] photocycloaddition-fragmentation sequence was successfully developed to enable a conceptually new entry to cis-fused lycorine-type alkaloids of the Amaryllidaceae family. Hence, the cis-selective annulation of six-membered rings on isoquinolones was successfully accomplished by employing cyclobutenes as olefin components and a variety of substitution patterns was accessible by this simple two step procedure. During our investigation we found the high ring strain of bicyclo[2.2.0]hexanes and a donor-acceptor substitution pattern to be crucial for successful transformation.