An Acyl Radical Cascade Model for the Total Synthesis of Lyconadin A

Lyconadin A (1) is a structurally unique Lycopodium alkaloid with antitumor properties, isolated from the club moss Lycopodium complanatum. We are developing a synthetic route to 1 based on a novel 7-exo-trig/6-exo-trig acyl radical cascade cyclization. The synthesis of model acyl radical cascade precursor 23 will be presented. Key features of this synthesis include the suppression of competing elimination during the alkylation of a hindered phenethyl bromide and the use of a lactone as a precursor to a compound bearing two differentially protected primary alcohols. An account of our studies on the model acyl radical cascade cyclization (23 to 24 above) will also be given, including a stereochemical analysis of the product. Our findings have been applied to develop a more detailed stereoselective synthetic plan for Lyconadin A (1).

Name thesis:degree_name

MS

Grantor dc:publisher

Brigham Young University - Provo

Author dc:creator

• Grant, Seth W.

• Lyconadin A
• lycopodium alkaloids
• acyl radical
• radical cascade
• 7-exo-trig
• radical cyclization
• total synthesis
• Biochemistry
• Chemistry

Language dc:language

English

Repository record dc:identifier

https://scholarsarchive.byu.edu/etd/759

OAI identifier oai:identifier

oai:scholarsarchive.byu.edu:etd-1758