Model Studies Towards the Total Synthesis of Lyconadin A via An Acyl Radical Cascade Reaction

Lyconadin A is an alkaloid possessing a unique structure and antitumor activity. The total synthesis of Lyconadin A was proposed via an acyl radical cascade reaction. To investigate the possibility and stereoselectivity of the cascade cyclization, phenyl selenoester 16 was chosen as a model substrate to study the 7-exo-5-exo radical cyclization. A synthetic route to phenyl selenoester 16 was developed. The 7-exo-5-exo radical cyclization was found to occur with a high yield and excellent stereoselectivty. Attempts were also tried to synthesize another radical precursor 14 albeit with less success. A synthetic pathway to the synthesis of 14 as well as its potential use in the context of the synthesis of Lyconadin A was proposed.

Name thesis:degree_name

MS

Grantor dc:publisher

Brigham Young University - Provo

Author dc:creator

• Zhu, Koudi

• Lyconadin A
• total synthesis
• 7-exo-5-exo radical cascade cyclization
• Biochemistry
• Chemistry

Language dc:language

English

Repository record dc:identifier

https://scholarsarchive.byu.edu/etd/478

OAI identifier oai:identifier

oai:scholarsarchive.byu.edu:etd-1477