Academic department under which the project should be listed

CSM - Chemistry and Biochemistry

Faculty Sponsor Name

Christopher W. Alexander

Not applicable. No animal or human subjects used in this project.

Abstract (300 words maximum)

Tetrahydroquinolines (THQs) are a group biologically active of N-heterocyclic molecules derived from natural sources that have served as the basis for a variety of anti-bacterial, anti-parasitic, and anti-viral drugs. The 1,2,3,4-tetrahydroquinoline alkaloids, (Hancock alkaloids), Angustureine, Cuspareine, Galipeine and Galipinine, isolated from the bark of the Angostura tree found in Venezuela, have demonstrated anti-malaria activity, analgesic properties, and a range of enzyme inhibitory activity. This poster presents the results to synthesize tert-butyl(5-(2-iodoethyl)-2-methoxyphenoxy)dimethylsilane (tBIMDS) from 2-(4-hydroxyphenyl)ethanol (tyrosol). tBIMDS is a non-commercially available starting material that will be coupled with the alpha-amino-cycloalkylcuprate of N-tert-butyl-1-(3,4-dihydroquinolin-1(2H)-yl)methanimine as the key reaction step in our planned total synthesis of Galipeine.

Project Type

Poster

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Synthesis of tert-Butyl(5-(2-iodoethyl)-2-methoxyphenoxy)dimethylsilane; a Side Chain Precursor that is Required for the Total Synthesis of the Hancock Alkaloid, Galipeine

Tetrahydroquinolines (THQs) are a group biologically active of N-heterocyclic molecules derived from natural sources that have served as the basis for a variety of anti-bacterial, anti-parasitic, and anti-viral drugs. The 1,2,3,4-tetrahydroquinoline alkaloids, (Hancock alkaloids), Angustureine, Cuspareine, Galipeine and Galipinine, isolated from the bark of the Angostura tree found in Venezuela, have demonstrated anti-malaria activity, analgesic properties, and a range of enzyme inhibitory activity. This poster presents the results to synthesize tert-butyl(5-(2-iodoethyl)-2-methoxyphenoxy)dimethylsilane (tBIMDS) from 2-(4-hydroxyphenyl)ethanol (tyrosol). tBIMDS is a non-commercially available starting material that will be coupled with the alpha-amino-cycloalkylcuprate of N-tert-butyl-1-(3,4-dihydroquinolin-1(2H)-yl)methanimine as the key reaction step in our planned total synthesis of Galipeine.