Synthesis of (+)-cananodine
Research Mentor(s)
Dr. James Vyvyan
Description
The goal of this graduate research project is to complete a multi-step synthesis to achieve the assembly of cananodine, a member of the guaipyridine alkaloid family, which is a biologically active molecule likely beneficial in treating liver cancer, specifically hepatocellular carcinoma (HCC). This disease is projected to affect over one million people annually by 2025 but existing therapies are expensive and not particularly effective. This synthetic route features a novel approach using an enantioselective redox-relay Heck reaction that builds off of excellent work accomplished by students in previous years who set the stage for the ultimate successful formation of the guaipyridine skeleton. Starting with simple, commercially available starting materials and using carefully chosen modern catalysts, this optically active molecule will be produced. Setting two unique stereocenters along a seven-membered carbocycle is a tricky and interesting challenge but it is imperative that progress is made in developing new compounds to change the way HCC is treated in the future.
Document Type
Event
Start Date
May 2022
End Date
May 2022
Location
Carver Gym (Bellingham, Wash.)
Department
CSE - Chemistry
Genre/Form
student projects; posters
Type
Image
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.
Language
English
Format
application/pdf
Synthesis of (+)-cananodine
Carver Gym (Bellingham, Wash.)
The goal of this graduate research project is to complete a multi-step synthesis to achieve the assembly of cananodine, a member of the guaipyridine alkaloid family, which is a biologically active molecule likely beneficial in treating liver cancer, specifically hepatocellular carcinoma (HCC). This disease is projected to affect over one million people annually by 2025 but existing therapies are expensive and not particularly effective. This synthetic route features a novel approach using an enantioselective redox-relay Heck reaction that builds off of excellent work accomplished by students in previous years who set the stage for the ultimate successful formation of the guaipyridine skeleton. Starting with simple, commercially available starting materials and using carefully chosen modern catalysts, this optically active molecule will be produced. Setting two unique stereocenters along a seven-membered carbocycle is a tricky and interesting challenge but it is imperative that progress is made in developing new compounds to change the way HCC is treated in the future.